Hydrochloric Acid → 2-(4-Chlorophenyl)-N-[4-(dimethylamino)phenyl]-N-methyl-3H-imidazo[4,5-b]pyridine-3-acetamide hydrochloride hydrate

HRID 623085Notes

Reaction equation

HRID 623085 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([N:20]([C:22]3[CH:27]=[CH:26][C:25]([N:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=3)[CH3:21])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.Cl.C(OC(C)C)(C)C>C(O)(C)C>[OH2:19].[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([N:20]([C:22]3[CH:23]=[CH:24][C:25]([N:28]([CH3:30])[CH3:29])=[CH:26][CH:27]=3)[CH3:21])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 143903702-(4-Chlorophenyl)-N-[4-(dimethylamino)phenyl]-N-methyl-3H-imidazo [4,5-b]pyridine-3-acetamide

Product 1

HCID 230374202-(4-Chlorophenyl)-N-[4-(dimethylamino)phenyl]-N-methyl-3H-imidazo[4,5-b]pyridine-3-acetamide hydrochloride hydrateYield 118.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of 2-(4-chlorophenyl)-N-[4-(dimethylamino)phenyl]-N-methyl-3H-imidazo[4,5-b]pyridine-3-acetamide (5.6 g, 0.0133 mole) is hot isopropyl alcohol was acidified with hydrogen chloride in isopropyl alcohol. Isopropyl ether was added to precipitate a solid. The solid was collected by filtration, rinsed with isopropyl ether, and dried under high vacuum to give 3.74 g (52%) of title compound, mp 120°-132° C. (shrinks), 150°-155° C. (melts).

Workup

  1. customto precipitate a solid
  2. filtrationThe solid was collected by filtration
  3. washrinsed with isopropyl ether
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-d8a93b86646f46d9ae3b8115c48f13dd
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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