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

HRID 1290170Notes

Reaction equation

HRID 1290170 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-2bf8fdcca0864bd298dd8181c3483414
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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