HCID 70921731, compound → HCID 86660484, compound

HRID 2069126Notes

Reaction equation

HRID 2069126 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[CH3:23])[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]([CH3:23])[CH:16]=1

Participants

6

Reactant 2

HCID 70921731HCID 70921731, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86660484HCID 86660484, compound

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2-methoxy-N-(4-(2-methyl-4-nitrophenoxy)pyridin-2-yl)acetamide (357 mg, estimated purity 92%, 1.04 mmol) in a mixture of MeOH (20 mL) and AcOH (2.0 mL) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, 25° C., 55 mm 10% Pt/C Cat-Cart, full hydrogen mode) and was then evaporated in vacuo. The residue was taken up into a mixture of MeOH (20 mL) and AcOH (2 mL) and re-subjected to hydrogenation under the same flow conditions, at an elevated temperature (1.0 mL min−1, 40° C., 55 mm 10% Pt/C Cat-Cart, full hydrogen mode). The mixture was concentrated by evaporation in vacuo to afford the title compound, Intermediate H2, as a viscous liquid; Rt 1.05 min (Method 1); m/z 288 (M+H)+ (ES+); which was used directly in the next step (below).

Workup

  1. customwas then evaporated in vacuo
  2. additionThe residue was taken up into a mixture of MeOH (20 mL) and AcOH (2 mL)
  3. customre-subjected to hydrogenation under the same flow conditions, at an elevated temperature (1.0 mL min−1, 40° C., 55 mm 10% Pt/C Cat-Cart, full hydrogen mode)
  4. concentrationThe mixture was concentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-cd68cf1c9cca4f78a577f8a26e46d6b5
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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