HCID 19261492, compound → HCID 16641022, compound

HRID 1357378Notes

Reaction equation

HRID 1357378 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[C:5](=[CH:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-])=O)=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]>[Pd].C(Cl)Cl>[CH3:1][O:2][C:3](=[O:24])[C:4]1[C:5](=[CH:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH2:21])=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 19261492HCID 19261492, compound

Product 1

HCID 16641022HCID 16641022, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2-nitrophenoxy)phthalic acid dimethyl ester (2.16 g, 6.53 mmol) and palladium on activated charcoal (10% Pd, 120 mg) in methylene chloride (115 ml) was hydrogenated in a Parr apparatus at 207 kPa (30 psi) for 16 hours. The mixture was filtered and evaporated to dryness in vacuo to give 4-(2-aminophenoxy)phthalic acid dimethyl ester as an yellow oil (yield: 1.88 g (96%)). 1H—NMR (CDCl3) in ppm: δ 3.86 (3H,s); 3.90 (3H, s); 6.7-6.97 (3H,m); 7.0-7.1 ( 2H,m); 7.15 (1H,d); 7.78 (1H,d). 13C—NMR (CDCl3) in ppm: δ 52.9; 53.2; 116.5; 117.4; 118.2; 119.4; 121.6; 124.4; 126.7; 132.1; 136.1; 139.2; 141.6; 160.8; 167.1; 168.8.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-958b5eef79c24383b8b00e8675aa186d
Source dataset
uspto-grants-2003_07
Patent number
US06590118B1

Reaction notes

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