Ethanol → n-(5-Amino-2-methoxyphenyl)acetamide

HRID 275446

Reaction equation

HRID 275446 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:4]=1[NH2:5].[CH3:13][C:14](O)=[O:15].CC(OC(C)=O)=O.CCO>O.C1COCC1.O=[Pt]=O>[C:14]([NH:5][C:4]1[CH:6]=[C:7]([CH:8]=[CH:9][C:3]=1[O:2][CH3:1])[NH2:10])(=[O:15])[CH3:13]

Participants

6

Reactant 3

HCID 702EthanolHCID 74472-Methoxy-5-nitroanilineHCID 21895370AcOH AcOAc

Product 1

HCID 267867n-(5-Amino-2-methoxyphenyl)acetamide

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

2-Methoxy-5-nitroaniline was purchased and acetylated using HOAc/Ac2O in H2O/THF according to known procedures to make 2-methoxy-5-nitroacetanilide. This was reduced using catalytic hydrogenation (PtO2, H2, EtOH) to afford 3-acetamido-4-methoxyaniline which was reacted as described in Examples 1 and 2 to yield the desired glutarimide.

Sources & evidence

ORD record
ord-a425c07c7b5d406baa6be5ac9f3e315a
Source dataset
uspto-grants-1995_02
Patent number
US05393735

Linked notes

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