Ammonium Acetate → 3-Aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, benzyl ester

HRID 328815Notes

Reaction equation

HRID 328815 reaction equation
O[CH:2]=[C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[CH:10]=2)[N:5]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH:4]1[CH3:28].C([O-])(=O)C.[NH4+:33]>C(O)C>[NH2:33][CH:2]=[C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[CH:10]=2)[N:5]([C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[CH:4]1[CH3:28]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 867338553-Hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, benzyl ester

Product 1

HCID 867339003-Aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, benzyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.0 g. of 3-hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, benzyl ester and 5.0 g. of ammonium acetate in 200 ml. of ethanol is heated to reflux for 35 min. The reaction is concentrated to dryness and the residue taken up in 200 ml. of chloroform. The chloroform solution is then washed successively with water (1 × 100 ml.), 1N aqueous sodium hdyroxide (2 × 100 ml.) and brine (1 × 100 ml.), dried over magnesium sulfate and concentrated to dryness. The residual oil is crystallized from ethyl acetate, 3.34 g., m.p. 143°-149.5° C. and 1.3 g. recrystallized from the same solvent, 660 mg., m.p. 144°-146.5° C.

Workup

  1. additionA mixture of 5.0 g
  2. temperatureto reflux for 35 min
  3. concentrationThe reaction is concentrated to dryness
  4. washThe chloroform solution is then washed successively with water (1 × 100 ml.), 1N aqueous sodium hdyroxide (2 × 100 ml.) and brine (1 × 100 ml.)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness
  7. customThe residual oil is crystallized from ethyl acetate, 3.34 g
  8. customrecrystallized from the same solvent, 660 mg

Sources & evidence

ORD record
ord-8e756caaa9e94ca2986b7b87856c1c96
Source dataset
uspto-grants-1977_04
Patent number
US04018758

Reaction notes

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