Sodium Bicarbonate → HCID 22459615, compound

HRID 604885Notes

Reaction equation

HRID 604885 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22459644HCID 22459644, compound

Product 1

HCID 22459615HCID 22459615, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 350 mg (1.6 mmol) 1-(2-methoxy-4-nitro-phenyl)-1H-imidazole and 1873 mg (8.3 mmol) stannous dichloride in ethyl acetate (5 ml) and ethanol (2.5 ml) were heated to 70° for 35 minutes. The reaction was poured onto water/ice and neutralized with an aqueous solution of sodium hydrogen carbonate. It was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulphate, filtered and the solvent was evaporated under reduced pressure to yield 255 mg (84%) 3-methoxy-4-(imidazol-1-yl)-phenylamine as a brown solid. MS ISP (m/e): 190.0 (100) (M+H)+.

Workup

  1. additionThe reaction was poured onto water/ice
  2. extractionIt was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-07a0beaae3544e5cb01cb843b5f55d04
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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