HCID 12052631, compound → HCID 12052632, compound

HRID 1264084Notes

Reaction equation

HRID 1264084 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-])=O.[H][H]>O=[Pt]=O.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:6][NH:7][C:8]1[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 12052631HCID 12052631, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12052632HCID 12052632, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

The title compound was prepared by the addition of Adam's catalyst (160 mg, 10% wt.) to a degassed solution of N-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]-2-nitroaniline (1.6 g, 4.69 mmol) in absolute ethanol (25 mL). The atmosphere was replaced with hydrogen then the reaction was stirred vigourously at ambient temperature until all of the nitro compound had been consumed as determined by tlc (9:1 CHCl3:MeOH, 1% TEA). The reaction mixture was filtered through a bed of diatomaceous earth, then the solvent was removed under reduced pressure to give the diamine as a brown yellow oil (1.46 g, 100%).

Workup

  1. customhad been consumed
  2. filtrationThe reaction mixture was filtered through a bed of diatomaceous earth
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6d31da48414c44ab97016609492f449c
Source dataset
uspto-grants-2003_04
Patent number
US06541499B1

Reaction notes

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