Water → 3-amino-N-(3-isopropyl-phenyl)-4-methyl-benzamide

HRID 446265

Reaction equation

HRID 446265 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-])=O.O.[CH:15]([C:18]1[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=1)([CH3:17])[CH3:16]>C1COCC1>[NH2:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[CH3:1])[C:6]([NH:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH:15]([CH3:17])[CH3:16])[CH:19]=1)=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 663234-Methyl-3-nitrobenzoyl chlorideHCID 4586793-Isopropylaniline

Product 1

HCID 251022283-amino-N-(3-isopropyl-phenyl)-4-methyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methyl-3-nitro-benzoyl chloride (2.00 g, 0.010 mol) in THF (30 mL), in a water bath-cooled 100 mL round bottom flask, was added 3-isopropyl-phenylamine (1.35 g, 0.010 mol) dropwise. The reaction was allowed to stir at room temperature for 1 hour before being concentrated. The mixture was taken up in EtOAc and washed with NaHCO3 (aq., conc.) and then brine. The solution was dried over MgSO4, filtered, and concentrated to yield the title compound as an orange oil that solidifies upon standing. MS m/z 299=[M+H]+. Calc'd for C17H18N2O3: 298.34.

Workup

  1. concentrationbefore being concentrated
  2. washwashed with NaHCO3 (aq., conc.)
  3. dry with materialThe solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5de080ae1653465bae986fad0389e8c9
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Linked notes

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