Pyridine → N-(2-hydroxy-5-nitrophenyl)butanamide

HRID 1896786

Reaction equation

HRID 1896786 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].N1C=CC=CC=1.[C:18](Cl)(=[O:22])[CH2:19][CH2:20][CH3:21]>ClCCl>[OH:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[NH:1][C:18](=[O:22])[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 3599768N-(2-hydroxy-5-nitrophenyl)butanamideYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-4-nitrophenol (10 g, 64.9 mmol) in dichloromethane (250 mL) under nitrogen at 0° C. was added pyridine (10.5 mL, 129.9 mmol) followed by butyryl chloride (7.05 mL, 68.2 mmol) over a period of 5 min. After 30 min at 0° C., the solution was left warming up to room temperature for 2 days. The organic layer was washed with aqueous copper sulfate solution and brine. Insoluble material from the aqueous layer was filtered off and washed with water to afford 4.95 g (34%) of the title compound.

Workup

  1. waitthe solution was left
  2. washThe organic layer was washed with aqueous copper sulfate solution and brine
  3. filtrationInsoluble material from the aqueous layer was filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-dbfe4d536cbc491a93d8c0c88be0fe2a
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Linked notes

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