Toluene → HCID 18184944, compound

HRID 1358587Notes

Reaction equation

HRID 1358587 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:24]([O-])=O)=[C:13]([N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:14]=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Pd].CO>[NH2:24][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][C:13]=1[N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21]

Participants

5

Reactant 2

HCID 1140TolueneHCID 18184950HCID 18184950, compound

Product 1

HCID 18184944HCID 18184944, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of t-butyl N-(5-benzyloxy-2-nitrophenyl)-N-methylcarbamate (15 g), palladium on carbon (3 g, 10%), toluene (150 ml) and methanol (150 ml) was stirred under a hydrogen atmosphere at room temperature for 12.5 hours. The palladium on carbon was filtered and the filtrate was concentrated to afford the title compound (12.3 g, brown oil, Rf=0.15: thin layer chromatography on a silica gel plate using hexane: ethyl acetate=4 : 1 as the eluant).

Workup

  1. filtrationThe palladium on carbon was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2119d44e4ccf444b9a31710179899af8
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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