GB1153796A - A method of Preparing Substituted Benzamides - Google Patents

A method of Preparing Substituted Benzamides

Info

Publication number
GB1153796A
GB1153796A GB50701/66A GB5070166A GB1153796A GB 1153796 A GB1153796 A GB 1153796A GB 50701/66 A GB50701/66 A GB 50701/66A GB 5070166 A GB5070166 A GB 5070166A GB 1153796 A GB1153796 A GB 1153796A
Authority
GB
United Kingdom
Prior art keywords
compound
phenol
nitro
amino
halo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB50701/66A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Societe dEtudes Scientifiques et Industrielles de lIle de France SA
Original Assignee
Societe dEtudes Scientifiques et Industrielles de lIle de France SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Societe dEtudes Scientifiques et Industrielles de lIle de France SA filed Critical Societe dEtudes Scientifiques et Industrielles de lIle de France SA
Publication of GB1153796A publication Critical patent/GB1153796A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/50—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups

Abstract

1,153,796. Substituted benzamides. SOC. D'ETUDES SCIENTIFIQUES ET INDUSTRIELLES DE L'ILE-DE-FRANCE. 11 Nov., 1966 [27 Dec., 1965], No. 50701/66. Heading C2C. A substituted benzamide of general formula in which A is hydrogen, a C 1 -C 5 alkyl group or a C 2 -C 5 alkenyl group; X is amino, alkylamino, dialkylamino or acylamino radical; Y is a halogen atom; and n is 1, 2 or 3 and in which one of the -CH 2 - groups in A or the carboxamide group may be branched to form the group in which R 3 is a radical containing 1-4 carbon atoms and in which R 1 and R 2 are identical or different C 1 -C 5 alkyl groups or together with the nitrogen atom to which they are attached form a heterocyclic ring, may be prepared by nitrating a p-halogeno-phenol to form the 2-nitro-4-halo-phenol; optionally alkylating or alkenylating thio to form a 2-nitro-4-haloalkoxy or alkenyloxy benzene; reducing the 2- nitro - 4 - halo - phenol or alkoxy or alkenoxy phenol to the corresponding amino compound, acylating the amino compound to form the 2- acetylamino - 4 - halo - phenol, alkoxyphenol or alkenyloxyphenol; nitrating the 2-acetylamino compound to form the corresponding 2-acetylamino - 4 - halo - 5 - nitro compound; hydrolysing this to form the 2-amino compound; diazotizing this compound and treating the product with cuprous cyanide to form the corresponding 2-cyano compound; hydrolysing the cyano compound and heating with an alcohol to get the corresponding alkyl ester; heating this with an asymmetrically disubstituted diamine to get the corresponding N-(tertiary amino alkyl)-benzamide and reducing and optionally alkylating or acylating the nitro group. An example is given of the preparation of N - (diethyl aminoethyl) - 2 - methoxy - 4- amino-5-chlorobenzamide and its conversion to its hydrochloride.
GB50701/66A 1965-12-27 1966-11-11 A method of Preparing Substituted Benzamides Expired GB1153796A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR43874A FR1513226A (en) 1965-12-27 1965-12-27 New process for the preparation of substituted benzamides

Publications (1)

Publication Number Publication Date
GB1153796A true GB1153796A (en) 1969-05-29

Family

ID=8596948

Family Applications (1)

Application Number Title Priority Date Filing Date
GB50701/66A Expired GB1153796A (en) 1965-12-27 1966-11-11 A method of Preparing Substituted Benzamides

Country Status (9)

Country Link
JP (1) JPS546539B1 (en)
BE (1) BE688790A (en)
CH (1) CH475949A (en)
DE (1) DE1543893C3 (en)
ES (1) ES333713A1 (en)
FR (1) FR1513226A (en)
GB (1) GB1153796A (en)
IL (1) IL26895A (en)
OA (1) OA02159A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4250110A (en) 1978-07-31 1981-02-10 Asahi Kasei Kogyo Kabushiki Kaisha Method of preparing metoclopramide
US4279836A (en) * 1978-05-12 1981-07-21 Asahi Kasei Kogyo Kabushiki Kaisha Hydroxamic acid derivative and method of preparing metoclopramide using same
CN111349052A (en) * 2020-04-07 2020-06-30 福建海西新药创制有限公司 Synthesis method of mosapride citrate

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2460923A1 (en) * 1979-07-06 1981-01-30 Ile De France Prepn. of psychotropic drug intermediates - from 3-nitro-4-amino:anisole by five-stage process to 2-methoxy-4-amino-5-alkyl sulphonyl:benzoic acids

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4279836A (en) * 1978-05-12 1981-07-21 Asahi Kasei Kogyo Kabushiki Kaisha Hydroxamic acid derivative and method of preparing metoclopramide using same
US4250110A (en) 1978-07-31 1981-02-10 Asahi Kasei Kogyo Kabushiki Kaisha Method of preparing metoclopramide
US4297503A (en) 1978-07-31 1981-10-27 Asahi Kasei Kogyo Kabushiki Kaisha Novel benzamide derivative and method of preparing metoclopramide using same
CN111349052A (en) * 2020-04-07 2020-06-30 福建海西新药创制有限公司 Synthesis method of mosapride citrate
CN111349052B (en) * 2020-04-07 2021-02-12 福建海西新药创制有限公司 Synthesis method of mosapride citrate

Also Published As

Publication number Publication date
DE1543893B2 (en) 1974-10-10
DE1543893C3 (en) 1975-05-22
CH475949A (en) 1969-07-31
JPS546539B1 (en) 1979-03-29
ES333713A1 (en) 1967-10-01
IL26895A (en) 1971-08-25
DE1543893A1 (en) 1970-02-05
OA02159A (en) 1970-05-05
BE688790A (en) 1967-04-24
FR1513226A (en) 1968-02-16

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