Methyl 4-[4-(tert-Butyldimethylsilyloxy)-2-nitrophenylamino]methyl-2-methoxybenzoate → HCID 12052621, compound

HRID 1264070Notes

Reaction equation

HRID 1264070 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([O:27][CH3:28])[CH:18]=2)=[C:11]([N+:29]([O-])=O)[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>O=[Pt]=O.CCO>[NH2:29][C:11]1[CH:10]=[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:14]=[CH:13][C:12]=1[NH:15][CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([O:27][CH3:28])[CH:18]=1

Participants

4

Reactant 1

HCID 12052620Methyl 4-[4-(tert-Butyldimethylsilyloxy)-2-nitrophenylamino]methyl-2-methoxybenzoate

Product 1

HCID 12052621HCID 12052621, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To the above nitro compound (Example 1, Part C; 0.5 g, 1.11 mmol) was added PtO2 (Adam's) catalyst (0.025 g) and EtOH (absolute, 40 mL). The mixture was rapidly stirred under a hydrogen atmosphere (balloon) for 1.5 h and then the catalyst removed by filtering over a pad of diatomaceous earth. The filtrate was concentrated under reduced pressure, yielding 460 mg (99%) of the desired product.

Workup

  1. customthe catalyst removed
  2. filtrationby filtering over a pad of diatomaceous earth
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2be82280911e458d944039128f6baa38
Source dataset
uspto-grants-2003_04
Patent number
US06541499B1

Reaction notes

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