Acetyl chloride → HCID 20375746, compound

HRID 1448813Notes

Reaction equation

HRID 1448813 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH:7]=[CH:6][C:5]([C:9]([O:11]C)=[O:10])=[CH:4]1.[C:13](Cl)(=[O:15])[CH3:14].C(N(CC)CC)C>ClCCl>[C:13]([NH:2][CH:3]1[CH2:8][CH:7]=[CH:6][C:5]([C:9]([OH:11])=[O:10])=[CH:4]1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 20375732HCID 20375732, compound

Product 1

HCID 20375746HCID 20375746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 190 mg (1 m mole) of methyl 3-amino-1,5-cyclohexadienecarboxylate hydrochloride in 5 ml of dichloromethane is treated with 78 mg (1 m mole) of acetyl chloride and 202 mg (2 m mole) of triethylamine for 1 hour at 25° C. after which the solution is washed with water, dryed and concentrated. The residue is treated at 25° C. with 3 ml of methanol and 100 ml of sodium hydroxide in 200 ml of water for 3 hours then acidified and extracted with dichloromethane. The organic phase is dried and evaporated to afford 3-acetamido-1,5-cyclohexadiene carboxylic acid.

Workup

  1. washis washed with water
  2. concentrationconcentrated
  3. additionThe residue is treated at 25° C. with 3 ml of methanol and 100 ml of sodium hydroxide in 200 ml of water for 3 hours
  4. extractionextracted with dichloromethane
  5. customThe organic phase is dried
  6. customevaporated

Sources & evidence

ORD record
ord-9214698061d64c64ae8d2742030d7330
Source dataset
uspto-grants-1980_02
Patent number
US04187316

Reaction notes

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