Acetyl chloride → HCID 19392573, compound

HRID 704926Notes

Reaction equation

HRID 704926 reaction equation
CO[C:3]1[CH:27]=[CH:26][C:25]2[C:9]3[N:10]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:11]4[NH:12][CH2:13][CH2:14][CH2:15][C:16]=4[C:17](=[O:18])[C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=1.[C:28](Cl)(=[O:30])[CH3:29].C(N(CC)CC)C>C(Cl)Cl>[C:28]([N:12]1[C:11]2[N:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:9]3[C:25]4[CH:26]=[CH:27][CH:3]=[CH:4][C:5]=4[CH2:6][CH2:7][C:8]=3[C:17](=[O:18])[C:16]=2[CH2:15][CH2:14][CH2:13]1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14423276HCID 14423276, compound

Product 1

HCID 19392573HCID 19392573, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat 5,6,8,9,10,11-hexahydro-3-methoxy-12-phenyl-naphtho[1,2-b][1,8]naphthyridin-7(12H)-one (10 mmoles) with equimolar amounts of acetyl chloride and triethylamine dissolved in CH2Cl2 (10 ml) at 0°-25° C. for 3 days. Wash the resulting solution with aqueous NaHCO3 solution and with water, and dry the organic solution. Evaporate the CH2Cl2, and chromatograph the residue on silica gel. Elute the N-acetylated product with 2% MeOH in CHCl3, and crystallize it from isopropyl acetate/disopropyl ether to provide 11-acetyl-5,6,8,9,10,11-hexahydro-12-phenyl-naphtho[1,2-b][1,8]naphthyridin-7(12H)-one, m.p. 178.5°-182° C.

Workup

  1. washWash the resulting solution with aqueous NaHCO3 solution
  2. dry with materialwith water, and dry the organic solution
  3. customEvaporate the CH2Cl2, and chromatograph the residue on silica gel
  4. washElute the N-acetylated product with 2% MeOH in CHCl3
  5. customcrystallize it from isopropyl acetate/disopropyl ether

Sources & evidence

ORD record
ord-f22849f0da254490ba16e51fbae811c9
Source dataset
uspto-grants-1991_01
Patent number
US04988705

Reaction notes

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