Benzoic acid, 2-methoxy-5-nitro-, methyl ester → Methyl 5-amino-o-anisate

HRID 59242

Reaction equation

HRID 59242 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]>CO.[Pd]>[NH2:13][C:10]1[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 1

HCID 7020925Benzoic acid, 2-methoxy-5-nitro-, methyl ester

Product 1

HCID 89843Methyl 5-amino-o-anisateYield 85.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 2-methoxy-5-nitrobenzoate (20.0 g, 0.097 mol) in methanol (300 mL) and 10% Pd/C (5.0 g) was stirred under hydrogen atmosphere under 70-80 psi pressure in Parr apparatus for 4-5 h. The reaction mass was filtered and the obtained filtrate was concentrated to afford 15.0 g of desired product. 1H NMR (300 MHz, DMSO de): δ 3.67 (s, 3H), 3.74 (s, 3H), 4.96 (br s, 2H), 6.75 (dd, J=2.4 Hz, 1H), 6.85 (d, J=8.7 Hz, 1H), 6.92 (s, 1H); MS (in/z): 182.25 (M+H)+.

Workup

  1. filtrationThe reaction mass was filtered
  2. concentrationthe obtained filtrate was concentrated

Sources & evidence

ORD record
ord-cf07bdbdfcae4f409b36dcbb35f3b249
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

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