HCID 86702446, compound → HCID 59771160, compound

HRID 2203287Notes

Reaction equation

HRID 2203287 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:14][N+:15]([O-])=O)[CH2:10][N+:11]([O-])=O)=[CH:5][CH:4]=1.[H][H]>CO.[Pt](=O)=O>[CH3:1][NH:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH2:14][NH2:15])[CH2:10][NH2:11])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 86702446HCID 86702446, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59771160HCID 59771160, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-methyl-4-[2-nitro-1-(nitromethyl)ethyl]aniline (42.7 mg, 0.178 mmol, 83 mol % purity) and 25 mg platinum (IV) oxide in 4 mL MeOH contained in a pressure tube was reacted under 65 PSI hydrogen. After 20 hours the mixture was filtered past Celite and rinsed with MeOH. The MeOH solution of crude product was stored under N2 in the freezer and used as is for the next reaction (contained 16 mol % [4-(methylamino)phenyl]methanol impurity). 1H NMR (CD3OD) δ: 7.00-7.05 (m, 2H), 6.62-6.68 (m, 2H), 2.83-2.91 (m, 2H), 2.70-2.79 (m, 5H), 2.57-2.67 (m, 1H)

Workup

  1. customcontained in a pressure tube
  2. filtrationAfter 20 hours the mixture was filtered past Celite
  3. washrinsed with MeOH
  4. customas is for the next reaction (contained 16 mol % [4-(methylamino)phenyl]methanol impurity)

Sources & evidence

ORD record
ord-b1ca5907388545cf935864341b69e2be
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

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