GB629177A - Manufacture of new hydrazine compounds and derivatives thereof - Google Patents
Manufacture of new hydrazine compounds and derivatives thereofInfo
- Publication number
- GB629177A GB629177A GB36717/46A GB3671746A GB629177A GB 629177 A GB629177 A GB 629177A GB 36717/46 A GB36717/46 A GB 36717/46A GB 3671746 A GB3671746 A GB 3671746A GB 629177 A GB629177 A GB 629177A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrazino
- phthalazine
- pyridazine
- chloro
- yield
- 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
Links
Abstract
Hydrazino derivatives of compounds containing a pyridazine ring are prepared by substituting a group in the ortho position to a nitrogen atom in the pyridazine ring by a hydrazino group. The compounds containing a pyridazine ring may be pyridazine, pyridazines which are substituted with alkyl, aryl, aralkyl or substituted aromatic residues, or pyridazines having fused on aromatic or heterocyclic rings such as the phthalazines or pyrido-pyridazines. As substituents in the ortho position which can be substituted by a hydrazine group there may be used a halogen atom, an esterified hydroxy group, or a phenoxy or thioether group. Many examples of suitable starting materials are given. The hydrazine may or may not be substituted and one of the nitrogen atoms may form part of a heterocyclic ring, e.g. the piperidine or morpholine ring. The hydrazino derivatives formed may be converted into their salts, or they may be condensed with carbonyl compounds such as aldehydes or ketones. The following examples are given: (1) 1 - chlorophthalazine or 1-phenoxyphthalazine is heated with hydrazine hydrate in alcohol to yield 1-hydrazinophthalazine; (2) 1 - hydrazino - 4 - methylphthalazine is made by heating 1-chloro-4-methyl-phthalazine with hydrazine hydrate in alcohol; (3) 3-chloro-6-phenyl-pyridazine is heated with hydrazine hydrate in alcohol to yield 3-hydrazino-6-phenyl-pyridazine; (4) 3-chloro - 6 - methyl - pyridazine is heated with hydrazine hydrate in alcohol to yield 3-hydrazino - 6 - methyl - pyridazine; (5) 1 - chloro - 4-(p - methoxyphenyl) - phthalazine is heated with hydrazine hydrate in alcohol to yield 1-hydrazino - 4 - (p - methoxyphenyl) - phthalazine; (6) 1 - chloro - 4 - (p - dimethylaminophenyl) - phthalazine is treated as in (5) to yield 1 - hydrazino - 4 - (p - dimethylaminophenyl) - phthalazine; (7) 1 - hydrazinophthalazine is condensed with acetone in 2 N-acetic acid to yield the corresponding phthalazinyl - hydrazone of acetone; (8) 1 - chloro-4-benzyl-phthalazine is heated with hydrazine hydrate in alcohol to yield 1-hydrazino-4-benzyl-phthalazine; (9) 1-chloro-4-methyl-phthalazine is heated with methyl hydrazine to yield 1 - methylhydrazino - 4 - methyl-phthalazine; (10) 1 - hydrazino - phthalazine is condensed with formaldehyde in methanol to yield the phthalazinyl-hydrazone of formaldehyde; (11) 1-hydrazino-phthalazine is condensed with pyroracemic acid in methanol to give a compound of the formula <FORM:0629177/IV (b)/1> (12) b -benzoyl-picolinic acid (obtained from quinolinic anhydride and benzene in presence of aluminium chloride) is heated with hydrazine hydrate in water to yield phenyl-pyrido-pyridazine which is converted to the chloro compound with phosphorous oxychloride and then reacted with hydrazine hydrate in alcohol to give 6-hydrazino-3-phenyl-pyrido-21,31,4,5-pyridazine <FORM:0629177/IV (b)/2> (13) 1-chloro-4-phenyl-phthalazine is heated with hydrazine hydrate in alcohol to give 1-hydrazino-4-phenyl-phthalazene. The Specification as open to inspection under Sect. 91 comprises also the preparation of hydrazino derivatives of compounds containing a pyridazine ring by reducing a group, such as a nitroamino group, in the ortho position to a nitrogen atom in the pyridazine ring, and an example is given of the preparation of 1-hydrazino - 4 - methyl - phthalazine by reducing 1 - nitroamino 4 methyl - phthalazine (obtained by reacting 1-chloro-4-methyl-phthalazine with alcoholic ammonia and nitrating the product with fuming nitric acid in sulphuric acid) with zinc dust in caustic soda solution. It comprises also the treatment of the hydrazino derivatives of compounds containing a pyridazine ring with formic acid or chlorides or anhydrides of organic acids, and includes examples of the treatment of 1-hydrazino-phthalazine with acetyl chloride, formic acid and benzoyl chloride to give, respectively, compounds of the formul <FORM:0629177/IV (b)/3> This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH629177X | 1945-12-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB629177A true GB629177A (en) | 1949-09-14 |
Family
ID=4524622
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB36717/46A Expired GB629177A (en) | 1945-12-21 | 1946-12-12 | Manufacture of new hydrazine compounds and derivatives thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB629177A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4783461A (en) * | 1983-07-12 | 1988-11-08 | Gruppo Lepetit S.P.A. | 3,6-disubstituted triazolo [3,4-A]phthalazine derivatives |
US4788186A (en) * | 1982-01-18 | 1988-11-29 | Gruppo Lepetit S.P.A. | 6-substituted-s-triazolo[3,4-a]phthalazine derivatives |
US7807830B2 (en) | 2005-12-07 | 2010-10-05 | Navinta Llc | Manufacture of pure hydralazine salts |
CN110452133A (en) * | 2019-08-08 | 2019-11-15 | 贵州理工学院 | A kind of preparation method of diazanyl phthalic acid methyl ester derivative |
-
1946
- 1946-12-12 GB GB36717/46A patent/GB629177A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4788186A (en) * | 1982-01-18 | 1988-11-29 | Gruppo Lepetit S.P.A. | 6-substituted-s-triazolo[3,4-a]phthalazine derivatives |
US4783461A (en) * | 1983-07-12 | 1988-11-08 | Gruppo Lepetit S.P.A. | 3,6-disubstituted triazolo [3,4-A]phthalazine derivatives |
US7807830B2 (en) | 2005-12-07 | 2010-10-05 | Navinta Llc | Manufacture of pure hydralazine salts |
CN110452133A (en) * | 2019-08-08 | 2019-11-15 | 贵州理工学院 | A kind of preparation method of diazanyl phthalic acid methyl ester derivative |
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