2-methoxy-N-(4-(2-methoxy-4-nitrophenoxy)pyridin-2-yl)acetamide → N-(4-(4-Amino-2-methoxyphenoxy)pyridin-2-yl)-2-methoxyacetamide

HRID 2069132Notes

Reaction equation

HRID 2069132 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:15]=2[O:23][CH3:24])[CH:10]=[CH:9][N:8]=1)=[O:5].[H][H]>CO.CC(O)=O.[Pt]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][C:11]2[CH:10]=[CH:9][N:8]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][O:2][CH3:1])[CH:12]=2)=[C:15]([O:23][CH3:24])[CH:16]=1

Participants

6

Reactant 2

HCID 709217322-methoxy-N-(4-(2-methoxy-4-nitrophenoxy)pyridin-2-yl)acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 86660486N-(4-(4-Amino-2-methoxyphenoxy)pyridin-2-yl)-2-methoxyacetamide

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2-methoxy-N-(4-(2-methoxy-4-nitrophenoxy)pyridin-2-yl)acetamide (232 mg, 696 μmol) in a mixture of MeOH (30 mL) and AcOH (2.0 mL) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, 50° C., 55 mm 10% Pt/C Cat-Cart, full hydrogen mode) and was then evaporated in vacuo to afford the title compound, Intermediate H4 as an impure oily liquid; Rt 1.08 min (Method 2); m/z 304 (M+H)+ (ES+). This material, containing residual acetic acid was used directly, without further purification, in the next step (below).

Workup

  1. customwas then evaporated in vacuo

Sources & evidence

ORD record
ord-74fc1a0449c247968d779157ae2b2466
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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