Methyl Salicylate → 2-Hydroxybenzoic acid 2-(2-hydroxybenzoyl)hydrazide

HRID 465157

反応式

HRID 465157 の反応式
[C:1]([NH:10][NH2:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C[O:13][C:14](=O)[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:17].B(OB=O)=O>CO>[C:1]([NH:10][NH:11][C:14](=[O:13])[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:17])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

参加物

5

反応物 3

HCID 4133Methyl SalicylateHCID 13637Salicylic acid, hydrazideHCID 518682Boron trioxide

生成物 1

HCID 653032-Hydroxybenzoic acid 2-(2-hydroxybenzoyl)hydrazide収率 85%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

152 parts by weight salicyclic acid hydrazide was heated with 152 parts by weight salicylic-acid methyl ester and 3 parts by weight boron trioxide in 230 parts by weight paraffin (viscosity at 60° C.: 100 m Pa s) to 140° to 150° C. while stirring vigorously. Methanol produced during the reaction was distilled off by a column. After about 3 hours, the reaction was completed. The now viscous reaction mixture was cooled down to 50° to 60° C., treated with alcohol (methanol or ethanol) and the mixture was stirred very vigorously at about 50° to 60° C. The yellow-colored alcohol phase was decanted from the viscous paste and the process was repeated until discoloration was complete. After separating the washing alcohol, drying in a vacuum at about 100° C. was performed. 460 parts by weight of a colorless viscous paste was obtained, consisting of 230 parts by weight N,N'-bis(salicyloyl)hydrazine (85% yield) and 230 parts by weight paraffin. By dissolving the paraffin with methylene chloride and boiling-out the solid matter with methanol, N,N'-bis(salicyloyl)hydrazine with a melting and decomposition range of 305° to 310° C. was obtained.

後処理

  1. distillationwas distilled off by a column
  2. temperatureThe now viscous reaction mixture was cooled down to 50° to 60° C.
  3. additiontreated with alcohol (methanol or ethanol)
  4. stirringthe mixture was stirred very vigorously at about 50° to 60° C
  5. customThe yellow-colored alcohol phase was decanted from the viscous paste
  6. customAfter separating the washing alcohol
  7. customdrying in a vacuum at about 100° C.
  8. custom460 parts by weight of a colorless viscous paste was obtained

出典と根拠

ORDレコード
ord-d02fcdd517c04afbad5bc346503000b1
出典データセット
uspto-grants-1985_10
特許番号
US04550204

関連ノート

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