Benzoic acid, 3-methyl-2-nitro-, methyl ester → Methyl 3-methylanthranilate

HRID 490975

反応式

HRID 490975 の反応式
[CH3:1][C:2]1[C:3]([N+:12]([O-])=O)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]>[Pd].C(#N)C>[NH2:12][C:3]1[C:2]([CH3:1])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

参加物

4

反応物 1

HCID 79621Benzoic acid, 3-methyl-2-nitro-, methyl ester

生成物 1

HCID 2763406Methyl 3-methylanthranilate収率 97.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒2 回HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

Methyl 3-methyl-2-nitrobenzoate (98.5 g, 505 mmol), 5% Pd/C (Degussa CE 105 XRC/W, 1.0 g), and acetonitrile (300 mL) were combined in a 600-mL pressure vessel. The mixture was heated to 70° C. and hydrogenated at 65 psi (450 kPa) for 8 h. More 5% Pd/C (1.0 g) was added and hydrogenation was continued at 100 psi (690 kPa) for 8.5 h. Then the reaction mixture was cooled, purged with nitrogen, and filtered through Celite® diatomaceous filter aid, rinsing with acetonitrile (3×25 mL). The combined filtrates were partly evaporated to a weight of ˜160 g, and then diluted with acetonitrile to a total weight of 200g. Quantitative HPLC of this solution showed 40.3 wt % of the title compound (80.6 g, 97.5% yield).

後処理

  1. temperatureThen the reaction mixture was cooled
  2. custompurged with nitrogen
  3. filtrationfiltered through Celite® diatomaceous filter aid
  4. washrinsing with acetonitrile (3×25 mL)
  5. customThe combined filtrates were partly evaporated to a weight of ˜160 g
  6. additiondiluted with acetonitrile to a total weight of 200g

出典と根拠

ORDレコード
ord-ab13717415004796982f64776a49a673
出典データセット
uspto-grants-2009_05
特許番号
US07528260B2

関連ノート

読み込み中…