HCID 66889382, compound → HCID 66889371, compound

HRID 253269Notes

Reaction equation

HRID 253269 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([N+:17]([O-])=O)[C:14]=1[O:15][CH3:16])[C:8]([O:10][CH3:11])=[O:9])(=[O:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([NH2:17])[C:14]=1[O:15][CH3:16])[C:8]([O:10][CH3:11])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 66889382HCID 66889382, compound2×

Product 1

HCID 66889371HCID 66889371, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 3-(acetyloxy)-4-(methyloxy)-5-nitrobenzoate (27.2 g, 101 mmol.) in ethyl acetate (200 mL) with 10% palladium on carbon (1.0 g) added was hydrogenated at atmospheric pressure until complete reduction to the aniline was observed by TLC (>24 hours). The mixture was then filtered through a bed of celite and the filtrate concentrated to provide methyl 3-(acetyloxy)-5-amino-4-(methyloxy)benzoate (19.8 g, 82% yield) as an oil that slowly crystallized on standing. 1H NMR (400 MHz, CDCl3): 7.30 (d, 1H), 7.14 (d, 1H), 3.97 (br d, 2H), 3.85 (s, 3H), 3.82 (s, 3H), 2.34 (s, 3H).

Workup

  1. customwas observed by TLC (>24 hours)
  2. filtrationThe mixture was then filtered through a bed of celite
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-1b7ddabcd8534e37a38069c6b4e28994
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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