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

HRID 1284118ノート

反応式

HRID 1284118 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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 mixture 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 hydroxide (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.

後処理

  1. additionA mixture of 5.0 g
  2. temperatureto reflux for 35 min
  3. concentrationThe reaction mixture is concentrated to dryness
  4. washThe chloroform solution is then washed successively with water (1 × 100 ml.), 1N aqueous sodium hydroxide (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

出典と根拠

ORDレコード
ord-f73fe80336d44853a9443aad3f8e402e
出典データセット
uspto-grants-1976_08
特許番号
US03978064

反応ノート

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