HCID 13714010, compound → HCID 135736177, compound

HRID 4406Notes

Reaction equation

HRID 4406 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]([CH3:32])=[C:18]([CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=3)[N:19]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[O:16][C:17]([CH3:32])=[C:18]([CH2:20][CH2:21][O:22][C:23]3[CH:24]=[CH:25][C:26]([NH2:29])=[CH:27][CH:28]=3)[N:19]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 13714010HCID 13714010, compound

Product 1

HCID 135736177HCID 135736177, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-{2-[2-(4-benzyloxyphenyl)-5-methyl-4-oxazolyl]ethoxy}nitrobenzene (10.65 g) in methanol (200 ml) was subjected to a catalytic hydrogenation over 10% Pd-C (50% wet, 4.0 g). After the catalyst was filtered off, the filtrate was concentrated to give 4-{2-[2-(4-hydroxyphenyl)-5-methyl-4-oxazolyl]ethoxy}aniline (6.21 g, 78.2%). Recrystallization from methanol afforded brownish prisms, m.p. 184°-185° C. Elemental analysis for C18H18N2O3 ; Calcd.: C, 69.66; H, 5.85; N, 9.03. Found: C, 69.69; H, 5.87; N, 9.01.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a0c3c5e052b64fc395583abf06cf5d36
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Reaction notes

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