P-Anisidine → 2-Naphthalenecarboxamide, 4-amino-N-[4-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyl]-1-hydroxy-

HRID 263148Notes

Reaction equation

HRID 263148 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH2:29][CH3:30])([CH3:28])[CH3:27])=[CH:22][C:21]=1[C:31]([CH2:34][CH3:35])([CH3:33])[CH3:32])=[O:13].COC1C=CC([NH2:44])=CC=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>>[NH2:44][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([OH:1])=[C:3]([C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([CH2:29][CH3:30])([CH3:27])[CH3:28])=[CH:22][C:21]=2[C:31]([CH2:34][CH3:35])([CH3:33])[CH3:32])=[O:13])[CH:4]=1

Participants

4

Reactant 3

HCID 7732P-AnisidineHCID 24489Sodium DithioniteHCID 1225662-Naphthalenecarboxamide, N-[4-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyl]-1-hydroxy-

Product 1

HCID 30848622-Naphthalenecarboxamide, 4-amino-N-[4-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyl]-1-hydroxy-

Procedure

1-Hydroxy-N-[4-(2,4-di-t-pentylphenoxy)-butyl]-2-naphthamide was coupled with a diazotized p-anisidine ##STR29## The azo group of the compound thus prepared was then reduced with sodium dithionite (Na2S2O4) to the corresponding amine.

Workup

  1. customthus prepared

Sources & evidence

ORD record
ord-0aa4b877d78b4c20b4b0d20fc1f0e007
Source dataset
uspto-grants-1979_05
Patent number
US04156609

Reaction notes

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