Hydrochloric Acid → 8-(3-Amino-2,6-dichlorobenzyloxy)-3-bromo-2-methylimidazo[1,2-a]pyridine dihydrochloride

HRID 1899988Notes

Reaction equation

HRID 1899988 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N+:20]([O-])=O)[C:14]=3[Cl:23])[C:5]2=[N:4][C:3]=1[CH3:24].[ClH:25]>[Fe].CO>[ClH:19].[ClH:25].[NH2:20][C:15]1[C:14]([Cl:23])=[C:13]([C:18]([Cl:19])=[CH:17][CH:16]=1)[CH2:12][O:11][C:10]1[C:5]2[N:6]([C:2]([Br:1])=[C:3]([CH3:24])[N:4]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 117969163-Bromo-8-(2,6-dichloro-3-nitrobenzyloxy)-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 189233178-(3-Amino-2,6-dichlorobenzyloxy)-3-bromo-2-methylimidazo[1,2-a]pyridine dihydrochloride

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3-bromo-8-(2,6-dichloro-3-nitrobenzyloxy)-2-methylimidazo[1,2-a]pyridine (215 mg) and iron (powder, 84 mg) in a mixture of conc. hydrochloric acid (1 ml) and methanol (1 ml) was refluxed for half an hour. The cooled mixture was poured into an ice water (15 ml). The precipitates were collected and washed with water to give 8-(3-amino-2,6-dichlorobenzyloxy)-3-bromo-2-methylimidazo[1,2-a]pyridine dihydrochloride (140 mg) as an off-white solid.

Workup

  1. temperaturewas refluxed for half an hour
  2. customThe precipitates were collected
  3. washwashed with water

Sources & evidence

ORD record
ord-f9b79aa8d851478d9b7c7bdd9d89a3e9
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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