Acetic Acid → N-(3-amino-4-bromophenyl)-3-(2-cyanopropan-2-yl)benzamide

HRID 1184872Notes

Reaction equation

HRID 1184872 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([C:19]#[N:20])([CH3:18])[CH3:17])[CH:11]=2)=[CH:4][C:3]=1[N+:22]([O-])=O.C(O)(=O)C.C(O)C.C(#N)C>C1COCC1.[Zn]>[NH2:22][C:3]1[CH:4]=[C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([C:19]#[N:20])([CH3:17])[CH3:18])[CH:11]=2)[CH:6]=[CH:7][C:2]=1[Br:1]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 6342AcetonitrileHCID 67125575N-(4-bromo-3-nitrophenyl)-3-(2-cyanopropan-2-yl)benzamide

Product 1

HCID 67125603N-(3-amino-4-bromophenyl)-3-(2-cyanopropan-2-yl)benzamideYield 86.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

To a mixture of N-(4-bromo-3-nitrophenyl)-3-(2-cyanopropan-2-yl)benzamide 61 (400 mg, 1.030 mmol) and ZINC (1.011 g, 15.46 mmol) in THF (10 mL) at −5° C., acetic acid (1.180 mL, 20.61 mmol) was added. The reaction mixture was stirred at −5° C. for 30 min and 1 h at rt. Ethanol and acetonitrile were added and filtered off over filter. To the filtrate was added NaHCO3 solution and extracted with CH2Cl2. Organic layer was dried and evaporated to give crude N-(3-amino-4-bromophenyl)-3-(2-cyanopropan-2-yl)benzamide 62 (319 mg, 86%). (m/z)=358 and 360 (M+H)+.

Workup

  1. filtrationfiltered off
  2. filtrationover filter
  3. additionTo the filtrate was added NaHCO3 solution
  4. extractionextracted with CH2Cl2
  5. customOrganic layer was dried
  6. customevaporated

Sources & evidence

ORD record
ord-2682e8bb729c4b25a90d867cc6781d34
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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