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

HRID 490975

반응식

HRID 490975 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

HCID 2763406Methyl 3-methylanthranilate수율 97.5%

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ab13717415004796982f64776a49a673
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528260B2

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