Acetyl chloride → HCID 20450114, compound

HRID 358006Notes

Reaction equation

HRID 358006 reaction equation
Cl.[NH2:2][C:3]1([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[CH2:4]1.C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27]>ClCCl>[C:26]([NH:2][C:3]1([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[CH2:4]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 20450110HCID 20450110, compound

Product 1

HCID 20450114HCID 20450114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-amino-6-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate hydrochloride (13.6 g., 50 mM) was suspended in dry dichloromethane (200 ml.). The suspension was stirred and cooled in ice, and dry triethylamine (16.8 ml., 120 mM) was added, followed by acetyl chloride (4.3 ml., 60 mM). The mixture was stirred at room temperature for 16 hr. The solvent was evaporated in vacuo and the residue was dissolved in a mixture of ethyl acetate (1 l.) and water (500 ml.). The mixture was separated and the organic phase was washed successively with water (500 ml.), 2N hydrochloric acid (2×500 ml.), water (500 ml.) and saturated brine (500 ml.). The organic phase was dried (Na2SO4) and the solvent evaporated in vacuo. The solid was crystallised from ethyl acetate/petroleum ether (b.p. 60°-80°) to give methyl 2-acetylamino-6-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate, m.p. 160°-1°.

Workup

  1. temperaturecooled in ice
  2. stirringThe mixture was stirred at room temperature for 16 hr
  3. customThe solvent was evaporated in vacuo
  4. dissolutionthe residue was dissolved in a mixture of ethyl acetate (1 l.) and water (500 ml.)
  5. customThe mixture was separated
  6. washthe organic phase was washed successively with water (500 ml.), 2N hydrochloric acid (2×500 ml.), water (500 ml.) and saturated brine (500 ml.)
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. customthe solvent evaporated in vacuo
  9. customThe solid was crystallised from ethyl acetate/petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-89577c7f054a4a4ba440b8dbe3f2ba4a
Source dataset
uspto-grants-1984_08
Patent number
US04464358

Reaction notes

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