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

HRID 1184815Notes

Reaction equation

HRID 1184815 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:22]=[CH:23][CH:24]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([N+:19]([O-])=O)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].CC(O)=O>C1COCC1.[Zn]>[NH2:19][C:14]1[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:22]=[CH:23][CH:24]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=2)[CH:17]=[CH:16][C:15]=1[CH3:18]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 671255393-(1-Cyano-1-methylethyl)-N-(4-methyl-3-nitro-phenyl)benzamide

Product 1

HCID 67125542N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamideYield 100.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 3-(2-cyanopropan-2-yl)-N-(4-methyl-3-nitrophenyl)benzamide 4 (27 g, 84 mmol) and CH3COOH (72 mL, 1.3 mol) in THF (300 mL) at rt was added zinc (1.68 mol, 109 g). The temperature was maintained at 20° C. by cooling with an ice bath. The reaction was stirred at 20° C. for 1 hour. After dilution with ether the organic layer was extracted with 1N NaOH solution, water, brine, dried and evaporated to give crude N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 5 (24.7 g, 100%). 1H-NMR (400 MHz, CDCl3) 1.77 (s, 6H), 2.15 (s, 3H), 3.68 (br s, 2H). 6.77 (dd, J=7.1 and 1.9 Hz, 1H), 7.02 (d, J=8.0 Hz, 1H), 7.27 (br s, 1H), 7.50 (t, J=8, 1H), 7.69 (m, 1H), 7.75 (m, 2H), 7.96 (m, 1H).

Workup

  1. temperatureby cooling with an ice bath
  2. extractionAfter dilution with ether the organic layer was extracted with 1N NaOH solution, water, brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-5267118142104c4a8220c394e2e392e6
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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