P-Phenylenediamine → N-(4-aminophenyl)butanamide

HRID 1375285Notes

Reaction equation

HRID 1375285 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.CN1CCOCC1.[C:16](Cl)(=[O:20])[CH2:17][CH2:18][CH3:19]>C(Cl)Cl>[NH2:7][C:4]1[CH:5]=[CH:6][C:1]([NH:8][C:16](=[O:20])[CH2:17][CH2:18][CH3:19])=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 7814P-PhenylenediamineHCID 79724-MethylmorpholineHCID 8855Butyryl chloride

Product 1

HCID 721131N-(4-aminophenyl)butanamideYield 37.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,4-phenylenediamine (0.5 g, 4.62 mmol) in anhydrous CH2Cl2 (15 mL) was added NMM (0.51 mL, 4.62 mmol). To the resulting mixture was added dropwise butyryl chloride (0.45 mL, 4.62 mmol) in anhydrous CH2Cl2 (5 mL) at 0° C., and stirred for 0.5 h. The reaction mixture was extracted with CH2Cl2 (20 mL) and washed with H2O (20 mL). The organic layer was dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography over silica gel (EtOAc:hexane=1:3) to give N-(4-aminophenyl)butyramide (KYJ3-006-2, 0.31 g, 36%) as a colorless oil.

Workup

  1. extractionThe reaction mixture was extracted with CH2Cl2 (20 mL)
  2. washwashed with H2O (20 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography over silica gel (EtOAc:hexane=1:3)

Sources & evidence

ORD record
ord-92c9587a25624274ba059df954d064ff
Source dataset
uspto-grants-2007_01
Patent number
US07166744B2

Reaction notes

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