Ammonium Acetate → Ethyl 2-amino-1,6,7,11b-tetrahydro-9,10-dimethoxy-4H-benzo[a]quinolizine-3-carboxylate

HRID 1244685Notes

Reaction equation

HRID 1244685 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:23][N:10]2[CH2:11][CH2:12][C:13]3[C:18]([CH:9]2[CH2:8][C:7]1=O)=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)=[O:5])[CH3:2].C([O-])(=O)C.[NH4+:29]>CO>[CH2:1]([O:3][C:4]([C:6]1[CH2:23][N:10]2[CH2:11][CH2:12][C:13]3[C:18]([CH:9]2[CH2:8][C:7]=1[NH2:29])=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 68621423Ethyl 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-oxo-2H-benzo[a]quinolizine-3-carboxylate

Product 1

HCID 59687294Ethyl 2-amino-1,6,7,11b-tetrahydro-9,10-dimethoxy-4H-benzo[a]quinolizine-3-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 9,10-dimethoxy-2-oxo-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-3-carboxylic acid ethyl ester (Helv. Chim. Acta 1958, 41, 119; 4.00 g, 12.0 mmol) and ammonium acetate (13.9 g, 180 mmol) in methanol was stirred 5 h at room temperature. After evaporation of the solvent the residue was partitioned between dichloromethane and 1 M aq. sodium hydroxide solution. The organic layer was dried (MgSO4), and triturated with heptane to afford the title compound (3.71 g, 93%). Off-white solid, MS (ISP) 333.2 (M+H)+.

Workup

  1. customAfter evaporation of the solvent the residue
  2. customwas partitioned between dichloromethane and 1 M aq. sodium hydroxide solution
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customtriturated with heptane

Sources & evidence

ORD record
ord-9fb54d6a719a43918d408fd9ef74e541
Source dataset
uspto-grants-2006_10
Patent number
US07122555B2

Reaction notes

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