HCID 19977470, compound → HCID 19977492, compound

HRID 1451111Notes

Reaction equation

HRID 1451111 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:18]([O-])=O)[C:12]=1[NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:6]([O:8][CH3:9])=[O:7])=[O:2]>C(O)C.[Pt]=O>[NH2:18][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([CH2:1][OH:2])[C:12]=1[NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 19977470HCID 19977470, compound

Product 1

HCID 19977492HCID 19977492, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

Methyl 3-formyl-4-[(methylsulfonyl)amino]-5-nitrobenzoate (2.0 g, 0.0066 mol) was dissolved in ethanol (50 mL) and hydrogenated at 30 psi in the presence of platinum oxide (Aldrich, 0.1 g) for 4 h. The catalyst was removed by filtration through Celite and the filtrate was concentrated to dryness. The residue was recrystallized from methanolethyl acetate-hexane to give 0.8 g (44%) of methyl 3-amino-5-hydroxymethyl-4-[(methylsulfonyl)amino]benzoate as a light brown powder, mp 150°-155° C.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was recrystallized from methanolethyl acetate-hexane

Sources & evidence

ORD record
ord-d089e6b589b84383ba9159fd65b636a2
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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