3-Nitro-5-(octadecyloxy)benzoic acid methyl ester → 3-Amino-5-(octadecyloxy)benzoic acid methyl ester

HRID 1110258Notes

Reaction equation

HRID 1110258 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=[C:6]([N+:29]([O-])=O)[CH:5]=1>[Pd].C1COCC1>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=[C:6]([NH2:29])[CH:5]=1

Participants

4

Reactant 1

HCID 536989543-Nitro-5-(octadecyloxy)benzoic acid methyl ester

Product 1

HCID 193890883-Amino-5-(octadecyloxy)benzoic acid methyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3.55 g of 3-nitro-5-(octadecyloxy)benzoic acid methyl ester and 0.75 g of 10% palladium on carbon in 100 ml of THF was shaken under an initial hydrogen pressure of 52 psi until uptake ceased after 1.5 hours. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure to give 3.28 g of pure 3-amino-5-(octadecyloxy)benzoic acid methyl ester.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated at reduced pressure

Sources & evidence

ORD record
ord-442c2d56145e401fb9be993122ddb862
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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