Methanol → methyl 4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-4-carboxylate dihydrochloride

Reaction equation

[ClH:1].Cl.[NH:3]1[C:11]2[CH2:10][CH2:9][NH:8][CH:7]([C:12]([OH:14])=[O:13])[C:6]=2[N:5]=[CH:4]1.O=S(Cl)[Cl:17].[CH3:19]O>>[ClH:17].[ClH:1].[CH3:19][O:13][C:12]([CH:7]1[C:6]2[N:5]=[CH:4][NH:3][C:11]=2[CH2:10][CH2:9][NH:8]1)=[O:14]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 679459443H,4H,5H,6H,7H-imidazo[4,5-c]pyridine-4-carboxylic acid dihydrochloride

Product 1

HCID 67946063methyl 4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-4-carboxylate dihydrochloride

Procedure

32.3 g (0.134 moles) of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylic acid dihydrochloride in 500 ml of methanol were treated below -5° C. with 16 ml (0.220 moles) of SOCl2.

Sources & evidence

ORD record: ord-fa449267843049aa83d815c58283bb92
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04999359

Reaction notes

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