GB635635A - Manufacture of substituted mononitronaphthalenes and substituted monoaminonaphthalenes - Google Patents

Manufacture of substituted mononitronaphthalenes and substituted monoaminonaphthalenes

Info

Publication number
GB635635A
GB635635A GB19141/47A GB1914147A GB635635A GB 635635 A GB635635 A GB 635635A GB 19141/47 A GB19141/47 A GB 19141/47A GB 1914147 A GB1914147 A GB 1914147A GB 635635 A GB635635 A GB 635635A
Authority
GB
United Kingdom
Prior art keywords
nitro
chloro
methoxynaphthalene
halogen
alcohol
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
GB19141/47A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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 Ciba AG filed Critical Ciba AG
Publication of GB635635A publication Critical patent/GB635635A/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
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Mononitro - 1 - halogen - 2 - alkoxynaphthalenes are prepared by the treatment of a 1-halogen-2-alkoxynaphthalene with a nitrating agent consisting of nitric acid alone, and isolating at least one of the resulting isomers. The halogen is e.g. chlorine and the alkoxy group e.g. methoxy or ethoxy. For the nitration, nitric acid is used alone or mixed with an inert organic solvent, e.g. chlorobenzene. Temperatures in the range 10-80 DEG C., particularly 40-60 DEG C., are preferred. The product consists of 6-, 8-, and 4-nitro-2-alkoxy-1-halogen-naphthalenes. The 6-nitro compounds (particularly when the alkoxy group is methoxy) may be isolated by making use of their insolubility in boiling alcohol; with higher alkoxy groups, crystallization alternately from alcohol and carbon disulphide may be necessary. The compounds may be separated by distillation, preferably in vacuo; further purification may be effected by crystallization from carbon disulphide. In the examples: (1) powdered 1-chloro-2-methoxynaphthalene is added to nitric acid (62 per cent), the temperature being maintained at e.g. 40 DEG C. by cooling, to yield on dilution with water a crude product which is extracted with boiling ethanol to leave a residue of 6-nitro-1-chloro-2-methoxynaphthalene. The latter is reduced in alcohol with iron and a little acid to give 6-amino-1-chloro-2-methoxynaphthalene. In example (2) a solution of 1 - chloro - 2 - methoxynaphthalene in chlorobenzene is nitrated at 40-60 DEG C. and 6 - nitro - 1 - chloro - 2 - methoxynaphthalene isolated from the product. The 2-ethoxy compound is prepared in a similar way, isolated by crystallization, and reduced to the 6-amino compound. Example (3) is similar to example (2), but in addition to the isolation of the 6-nitro derivative, the more alcohol-soluble isomers are fractionally distilled in vacuo, and after a crystallization procedure, the 4-nitro and 8-nitro isomers are also obtained. The latter 8-nitro isomer is reduced to the 8-amino compound; the 8-nitro-1-chloro-2-ethoxy-naphthalene may be prepared in a similar manner. The Specification as open to inspection under Sect. 91 refers to the use of nitration agents in general. This subject-matter does not appear in the Specification as accepted.
GB19141/47A 1946-07-26 1947-07-17 Manufacture of substituted mononitronaphthalenes and substituted monoaminonaphthalenes Expired GB635635A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH635635X 1946-07-26

Publications (1)

Publication Number Publication Date
GB635635A true GB635635A (en) 1950-04-12

Family

ID=4525076

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19141/47A Expired GB635635A (en) 1946-07-26 1947-07-17 Manufacture of substituted mononitronaphthalenes and substituted monoaminonaphthalenes

Country Status (1)

Country Link
GB (1) GB635635A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0108604A1 (en) * 1982-11-05 1984-05-16 Uniroyal, Inc. Preparation of mono-nitro aromatic compounds
WO1985002612A1 (en) * 1983-12-08 1985-06-20 General Electric Company Method for making n-substituted nitrophthalimides
WO1985002613A1 (en) * 1983-12-08 1985-06-20 General Electric Company Destruction of dnpi in an all nitric acid nitration process
WO1985002615A1 (en) * 1983-12-08 1985-06-20 General Electric Company Nitration of phthalic acid and phthalic anhydride using nitric acid
US4902809A (en) * 1983-12-08 1990-02-20 General Electric Company Method for making N-substituted nitrophthalimides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0108604A1 (en) * 1982-11-05 1984-05-16 Uniroyal, Inc. Preparation of mono-nitro aromatic compounds
WO1985002612A1 (en) * 1983-12-08 1985-06-20 General Electric Company Method for making n-substituted nitrophthalimides
WO1985002613A1 (en) * 1983-12-08 1985-06-20 General Electric Company Destruction of dnpi in an all nitric acid nitration process
WO1985002615A1 (en) * 1983-12-08 1985-06-20 General Electric Company Nitration of phthalic acid and phthalic anhydride using nitric acid
US4902809A (en) * 1983-12-08 1990-02-20 General Electric Company Method for making N-substituted nitrophthalimides

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