Ammonium Hydroxide → HCID 20355526, compound

HRID 371669Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]=[C:9]([C:12]([F:15])([F:14])[Cl:13])[N:10]([OH:11])[C:3]=12.[OH-].[NH4+:17]>>[NH2:17][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]=[C:9]([C:12]([F:15])([F:14])[Cl:13])[N:10]([OH:11])[C:3]=12

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 20355505HCID 20355505, compound

Product 1

HCID 20355526HCID 20355526, compound

Procedure

7-Chloro-1-hydroxy-2-(difluorochloromethyl)-1H-imidazo-(4,5-b)pyridine is reacted with ammonium hydroxide to obtain 7-amino-1-hydroxy-2-(difluorochloromethyl)-1H-imidazo(4,5-b)pyridine which is oxidized to the corresponding 7-nitro-1-hydroxy-2-(difluorochloromethyl)-1H-imidazo(4,5-b)pyridine. Also, the 7-amino-1-hydroxy-2-(difluorochloromethyl)-1H-imidazo(4,5-b)pyridine is treated with sodium nitrite and subsequently sodium cyanide to obtain the corresponding 7-cyano-1-hydroxy-2-(difluorochloromethyl)-1H-imidazo(4,5-b)pyridine. On treatment with 70 percent sulphuric acid the corresponding 7-carboxy-1-hydroxy-2-(difluorochloromethyl)-1H-imidazo(4,5-b)pyridine is prepared. On further treatment with SF4 and HF, there is obtained 7-(trifluoromethyl)-1-hydroxy-2-(difluorochloromethyl)-1H-imidazo(4,5-b)pyridine.

Sources & evidence

ORD record: ord-fd2b782a0a884d7d9c1a33d277135de9
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04087432

Reaction notes

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