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

HRID 490975

Reaction equation

[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]

Participants

Conditions

Temperature: 70 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-ab13717415004796982f64776a49a673
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528260B2

Linked notes

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