Methyl 5-nitro-2-(2-methoxy-6-methoxymethoxyphenyl)-benzoate → Methyl 5-amino-2-(2-methoxy-6-methoxymethoxyphenyl)-benzoate

HRID 2269799Notes

Reaction equation

HRID 2269799 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:14]2[C:19]([O:20][CH2:21][O:22][CH3:23])=[CH:18][CH:17]=[CH:16][C:15]=2[O:24][CH3:25])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:14]2[C:19]([O:20][CH2:21][O:22][CH3:23])=[CH:18][CH:17]=[CH:16][C:15]=2[O:24][CH3:25])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 1

HCID 18189455Methyl 5-nitro-2-(2-methoxy-6-methoxymethoxyphenyl)-benzoate

Product 1

HCID 18188782Methyl 5-amino-2-(2-methoxy-6-methoxymethoxyphenyl)-benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of Example 32A (10.0 g) and 10% Pd/C (1.0 g) in methanol (200 mL) at room temperature was hydrogenated at 4 atm for 1 hour, filtered through diatomaceous earth (Celite®), and concentrated to provide the desired product. MS (ESI(−)Q1MS) m/z 316 (M−H)−.

Workup

  1. filtrationfiltered through diatomaceous earth (Celite®)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c232fd25a5554fa7a446b8273a76a924
Source dataset
uspto-grants-2001_12
Patent number
US06329534B1

Reaction notes

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