Methyl 2-((3-methyl-4-nitroisothiazol-5-yl)carbamoyl)benzoate → Methyl 2-((4-amino-3-methylisothiazol-5-yl)carbamoyl)benzoate

HRID 1850699Notes

Reaction equation

HRID 1850699 reaction equation
[CH3:1][C:2]1[C:6]([N+:7]([O-])=O)=[C:5]([NH:10][C:11]([C:13]2[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=2[C:15]([O:17][CH3:18])=[O:16])=[O:12])[S:4][N:3]=1.[H][H]>CO.[Pd]>[NH2:7][C:6]1[C:2]([CH3:1])=[N:3][S:4][C:5]=1[NH:10][C:11]([C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16])=[O:12]

Participants

5

Reactant 2

HCID 90411396Methyl 2-((3-methyl-4-nitroisothiazol-5-yl)carbamoyl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 90411342Methyl 2-((4-amino-3-methylisothiazol-5-yl)carbamoyl)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-((3-methyl-4-nitroisothiazol-5-yl)carbamoyl)benzoate was suspended in MeOH (30 mL), Pd/C 10% (477.1 mg, 4.483 mmol) was added and the mixture was hydrogenated at RT under 1 atm of hydrogen (balloon pressure) for 2 h. The catalyst was filtered off and the mixture was concentrated in vacuo, yielding methyl 2-((4-amino-3-methylisothiazol-5-yl)carbamoyl)benzoate. (150 mg, 100%). MS (ES+) 292.1.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-7d8797577f3e4b8bb5a387b98543e0f7
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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