4-Isopropylaniline → 2-amino-N-(4-isopropylphenyl)benzamide

HRID 1846307Notes

Reaction equation

HRID 1846307 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])OC1=O.[CH:13]([C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)([CH3:15])[CH3:14]>CN(C=O)C>[NH2:1][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]([NH:20][C:19]1[CH:21]=[CH:22][C:16]([CH:13]([CH3:15])[CH3:14])=[CH:17][CH:18]=1)=[O:11]

Participants

4

Reactant 2

HCID 74644-IsopropylanilineHCID 8359Isatoic Anhydride

Product 1

HCID 28065462-amino-N-(4-isopropylphenyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1H-benzo[d][1,3]oxazine-2,4-dione (2.0 g, 12.2 mmol) and 4-isopropylaniline (1.92 mL, 13.5 mmol) in anhydrous DMF (10 mL) was stirred at 115° C. for 6 hours under nitrogen. DMF was removed and the residue was mixed with water (100 mL) and dichloromethane (150 mL). The organic phase was separated and washed with brine (50 mL). The solvent was removed and the residue was washed with ether (50 mL) to give 2-amino-N-(4-isopropyl-phenyl)-benzamide as a solid. Yield: 0.80 g (25.8%).

Workup

  1. customDMF was removed
  2. additionthe residue was mixed with water (100 mL) and dichloromethane (150 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (50 mL)
  5. customThe solvent was removed
  6. washthe residue was washed with ether (50 mL)

Sources & evidence

ORD record
ord-01fc900d4dd64fcbbf2c0b781848793e
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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