6-Methylanthranilic acid → Benzoic acid, 2-amino-6-methyl-, methyl ester

HRID 2353941Notes

Reaction equation

HRID 2353941 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][Si](C=[N+]=[N-])(C)C>C(OC(=O)C)C.C(O)C>[CH3:12][O:5][C:4](=[O:6])[C:3]1[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 1512106-Methylanthranilic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 583916Benzoic acid, 2-amino-6-methyl-, methyl esterYield 100.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2-Amino-6-methyl-benzoic acid (3.00 g, 19.8 mmol) in ethylacetate (100 mL) and ethanol (100 mL) and add (trimethylsilyl) diazomethane (19.8 mL, 39.7 mmol, 2M in hexane) at room temperature and stir the solution for 1 h 30 min. Remove the solvent under reduced pressure to afford the title compound (3.30 g, quantitative). 1H NMR (CDCl3, 300 MHz) δ 2.43 (s, 3H), 3.89 (s, 3H), 5.11 (brs, 2H), 6.52 (m, 2H), 7.08 (t, J=7.7 Hz, 1H). MS (ES+): 166 (M+H).

Workup

  1. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-5e369432f1384671acbacfdd4e6958ba
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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