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Methanol → t-butyl N-[2-amino-5-(4-hydroxyphenoxy)phenyl]-N-methylcarbamate

HRID 2303854
Notes
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Reaction equation

HRID 2303854 reaction equation
C([O:8][C:9]1[CH:33]=[CH:32][C:12]([O:13][C:14]2[CH:15]=[CH:16][C:17]([N+:29]([O-])=O)=[C:18]([N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:19]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CO>[Pd].O1CCOCC1>[NH2:29][C:17]1[CH:16]=[CH:15][C:14]([O:13][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:33][CH:32]=2)=[CH:19][C:18]=1[N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 887MethanolHCID 18461365t-Butyl N-[5-(4-benzyloxyphenoxy)-2-nitrophenyl]-N-methylcarbamate

Product 1

HCID 18461282t-butyl N-[2-amino-5-(4-hydroxyphenoxy)phenyl]-N-methylcarbamateYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

By using 3.32 g of t-butyl N-[5-(4-benzyloxyphenoxy)-2-nitrophenyl]-N-methylcarbamate, 0.39 g of 10% palladium on carbon, 100 ml of methanol and 100 ml of 1,4-dioxane, reaction and purification were carried out in a similar manner to that described in Reference Example 7, whereby 2.40 g of the title compound were obtained.

Sources & evidence

ORD record
ord-1bf8905182114a458f46eb3e8375b7ab
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06432993B1

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes