Butyric Acid → Butyranilide, 3'-hydroxy-

HRID 30542

Reaction equation

HRID 30542 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](O)(=[O:13])[CH2:10][CH2:11][CH3:12].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:9]([NH:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1)(=[O:13])[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 264Butyric AcidHCID 10868DicyclohexylcarbodiimideHCID 115683-Aminophenol

Product 1

HCID 30688Butyranilide, 3'-hydroxy-

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3-aminophenol (550 mg; 5 mmol) is added to a solution of butyric acid (1.4 mL; 15 mmol) in DCM (20 mL) at room temperature and stirred vigorously. To this solution DCC (2.48 g; 12 mmol) is added followed by DMAP (24 mg) and the contents stirred overnight at room temperature. The reaction mixture is then filtered and washed with DCM. The filtrate is concentrated and redissolved in methanol, added with 10% aqueous sodium bicarbonate solution and stirred vigorously until diacylated byproduct disappeared (as detected by LC-MS) to yield 3-butyramidophenol as the only product. The product was used for further transformation without further purification.

Workup

  1. stirringthe contents stirred overnight at room temperature
  2. filtrationThe reaction mixture is then filtered
  3. washwashed with DCM
  4. concentrationThe filtrate is concentrated
  5. dissolutionredissolved in methanol
  6. additionadded with 10% aqueous sodium bicarbonate solution
  7. stirringstirred vigorously until diacylated byproduct

Sources & evidence

ORD record
ord-f7fc558c37ee4ad39b47dd34e986dce7
Source dataset
uspto-grants-2008_09
Patent number
US07423177B2

Linked notes

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