Acetic Anhydride → HCID 14368490, compound

HRID 1762193Notes

Reaction equation

HRID 1762193 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:30]=[CH:29][CH:28]=[CH:27][C:10]=1[CH2:11][O:12][C:13]1[C:14]2[N:15]([C:19]([CH2:23][N:24]([CH3:26])[CH3:25])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1>C(Cl)Cl>[C:1]([NH:8][C:9]1[CH:30]=[CH:29][CH:28]=[CH:27][C:10]=1[CH2:11][O:12][C:13]1[C:14]2[N:15]([C:19]([CH2:23][N:24]([CH3:26])[CH3:25])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14368489HCID 14368489, compound

Product 1

HCID 14368490HCID 14368490, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.43 g) was added dropwise to a solution of 8-(2-aminobenzyloxy)-3-dimethylaminomethyl-2-methylimidazo[1,2 a]pyridine (1 g) in methylene chloride (13 ml) with ice cooling. After being stirred for 5 hours at room temperature the reaction solution was washed successively with aqueous sodium bicarbonate, water, and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (20 g) with a mixture of methylene chloride and methanol (50:1-20:1) as an eluent to give 8-(2-acetamidobenzyloxy)-3-dimethylaminomethyl-2-methylimidazo[1,2-a]pyridine (0.88 g)

Workup

  1. washwas washed successively with aqueous sodium bicarbonate, water, and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (20 g) with a mixture of methylene chloride and methanol (50:1-20:1) as an eluent

Sources & evidence

ORD record
ord-9da0b6d9fc0a43a287bc85290fe62570
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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