Ethyl Acetate → HCID 66918937, compound

HRID 2354204Notes

Reaction equation

HRID 2354204 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:30])=[C:11]([NH:13][C:14](=[O:29])[C:15]3[CH:20]=[C:19]([O:21][CH2:22][C:23]([CH3:25])=[CH2:24])[CH:18]=[CH:17][C:16]=3[N+:26]([O-])=O)[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.[BH4-].[Na+].C(OCC)(=O)C>CO.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[NH2:26][C:16]1[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]([CH3:25])=[CH2:24])=[CH:20][C:15]=1[C:14]([NH:13][C:11]1[CH:12]=[C:7]([C:5]([NH:4][CH:1]2[CH2:2][CH2:3]2)=[O:6])[CH:8]=[CH:9][C:10]=1[CH3:30])=[O:29]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 66918925N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-[(2-methylprop-2-en-1-yl)oxy]-2-nitrobenzamide

Product 1

HCID 66918937HCID 66918937, compoundYield 44.5%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-[(2-methylprop-2-en-1-yl)oxy]-2-nitrobenzamide (8.73 g) in methanol (250 ml) was added a saturated solution of copper acetate in water (80 ml). Sodium borohydride (4.3 g) was added portionwise and the mixture stirred for a further 1 hour at room temperature. Ethyl acetate (300 ml) was added and the mixture washed with aqueous sodium hydrogen carbonate (200 ml). The combined aqueous extracts were extracted with ethyl acetate (2×200 ml), the resulting organics washed with brine (100 ml) and dried (magnesium sulfate) and Concentrated to give the crude 2-amino-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-[(2-methylprop-2-en-1-yl)oxy]benzamide (3.6 g) as an oil which was used directly in the next step.

Workup

  1. washthe mixture washed with aqueous sodium hydrogen carbonate (200 ml)
  2. extractionThe combined aqueous extracts were extracted with ethyl acetate (2×200 ml)
  3. washthe resulting organics washed with brine (100 ml)
  4. dry with materialdried (magnesium sulfate)
  5. concentrationConcentrated

Sources & evidence

ORD record
ord-0197ef1af02647dcb69dfd3b1a8128c5
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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