Water → HCID 178487895, compound

HRID 2112101Notes

Reaction equation

HRID 2112101 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[NH:13][CH:14]=[C:15]([CH2:17][C:18](O)=[O:19])[N:16]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[NH:13][CH:14]=[C:15]([CH2:17][CH2:18][OH:19])[N:16]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 962WaterHCID 178487908HCID 178487908, compound

Product 1

HCID 178487895HCID 178487895, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.45 g (5.23 mmol) [2-(3-methoxy-4-nitro-phenyl)-1H-imidazol-4-yl]-acetic acid are dissolved in 36 ml THF and cooled to 0° C. and combined with 10 ml (18 mmol) borane-THF complex (1.8 mol/V). After 1 h the mixture is heated to 20° C. and stirred for 16 h. Water is added until the development of gas has ended. Then the mixture is extracted twice with saturated aqueous sodium hydrogen carbonate solution and ethyl acetate. The organic phases are combined, dried and freed from the solvent in vacuo.

Workup

  1. temperatureAfter 1 h the mixture is heated to 20° C.
  2. extractionThen the mixture is extracted twice with saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-756862ec6c424e9dab147694a5d8f477
Source dataset
uspto-grants-2009_04
Patent number
US07521457B2

Reaction notes

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