Sodium Cyanide → HCID 20355471, compound

HRID 371670Notes

Reaction equation

[N+]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[N:10]=[C:11]([C:14]([F:17])([F:16])[Cl:15])[N:12]([OH:13])[C:5]=12)([O-])=O.[NH2:18][C:19]1C=CN=C2N=C(C(F)(F)Cl)N(O)C=12.N([O-])=O.[Na+].[C-]#N.[Na+]>>[C:19]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[N:10]=[C:11]([C:14]([F:17])([F:16])[Cl:15])[N:12]([OH:13])[C:5]=12)#[N:18]

Participants

Reactant 4

HCID 8929Sodium Cyanide

HCID 20355457HCID 20355457, compound

HCID 20355526HCID 20355526, compound

HCID 23668193Sodium Nitrite

Product 1

HCID 20355471HCID 20355471, 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-c35faa0389d04786af9ac517370801e7
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04087432

Reaction notes

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