Benzoyl chloride, 3-nitro- → HCID 54295182, compound

HRID 1780506Notes

Reaction equation

HRID 1780506 reaction equation
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18].[N+:19]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26])([O-:21])=[O:20]>C1COCC1>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13]([NH:16][C:25](=[O:26])[C:24]4[CH:28]=[CH:29][CH:30]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18]

Participants

4

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 54185865HCID 54185865, compound

Product 1

HCID 54295182HCID 54295182, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 620 mg portion of (4aR)-(10bR)-4,10b-dimethyl-8-amino-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one was dissolved in 100 ml of THF, and an equivalent amount of 3-nitrobenzoyl chloride (500 mg) was added. The reaction mixture was stirred for 4 h, and was then evaporated to dryness under vacuum. The residue was purified by chromatography on silica gel, eluting with 10% methanol in ethyl acetate, and the product-containing fractions were evaporated and the resulting solid was crystallized from dichloromethane/hexane to obtain 595 mg of the desired product, m.p. 240°-242°. FDMS: m/e=393. α[D]589

Workup

  1. customwas then evaporated to dryness under vacuum
  2. customThe residue was purified by chromatography on silica gel
  3. washeluting with 10% methanol in ethyl acetate
  4. customthe product-containing fractions were evaporated
  5. customthe resulting solid was crystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-3644e195afb8485c8fe89e09b614ca9b
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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