Butylamine → 4-Butylamino-6-chloro-2-methyl-5-nitronicotinic acid ethyl ester

HRID 1973107ノート

反応式

HRID 1973107 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9]([Cl:16])=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1Cl)=[O:5])[CH3:2].[CH2:18]([NH2:22])[CH2:19][CH2:20][CH3:21].C(NC1C=C(Cl)NC(C)([N+]([O-])=O)C=1C(OCC)=O)CCC>CO.C(N(CC)CC)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9]([Cl:16])=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[NH:22][CH2:18][CH2:19][CH2:20][CH3:21])=[O:5])[CH3:2]

参加物

6

反応物 3

HCID 8007ButylamineHCID 12387594Ethyl 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylateHCID 867342334-Butylamino-6-chloro-2-methyl-2-nitropyridine-3-carboxylic acid, ethyl ester

生成物 1

HCID 123875984-Butylamino-6-chloro-2-methyl-5-nitronicotinic acid ethyl ester

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 8471Triethylamine溶媒

実験手順

139.5 g. of 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester (0.5 Mol.) are dissolved in about 500 ml. of methanol. 60 g. of triethylamine are added and the solution is heated at reflux temperature. At this point, 36.5 g. of n-butylamine are added dropwise. The solvent is then removed in vacuo and 500 ml. of benzene are added to the residue. The triethylamine hydrochloride is filtered off and the solvent evaporated. The resulting oil is dissolved in 300 ml. of methanol and yields on cooling 110 g. of 4-butylamino-6-chloro-2-methyl-2-nitropyridine-3-carboxylic acid, ethyl ester (70%), m.p. 33°-35° (methanol).

後処理

  1. temperaturethe solution is heated
  2. temperatureat reflux temperature
  3. customThe solvent is then removed in vacuo and 500 ml
  4. additionof benzene are added to the residue
  5. filtrationThe triethylamine hydrochloride is filtered off
  6. customthe solvent evaporated
  7. dissolutionThe resulting oil is dissolved in 300 ml
  8. customof methanol and yields
  9. temperatureon cooling 110 g

出典と根拠

ORDレコード
ord-2c88c7993f9b4719be9f08060b9f5eec
出典データセット
uspto-grants-1976_12
特許番号
US03996233

反応ノート

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