2-(4-Nitrophenyl)benzo[d]thiazol-6-yl acetate → 2-(4-Aminophenyl)benzo[d]thiazol-6-yl acetate

HRID 643647Notes

Reaction equation

HRID 643647 reaction equation
[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=3)[S:11][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]>C1COCC1.CO>[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=3)[S:11][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 592629692-(4-Nitrophenyl)benzo[d]thiazol-6-yl acetate

Product 1

HCID 589604502-(4-Aminophenyl)benzo[d]thiazol-6-yl acetateYield 72.9%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Under H2, 25 (2.7 mmol) was dissolved in a mixture of THF/MeOH (5/20 ml) and was then hydrogenated at room temperature for 1 h under 30 PSI. Pd (c) was filtered and the solvent removed via a rotary evaporator. The residue was purified by chromatography on silica gel using 7:3 hexane/ethyl acetate as the eluent to yield 560 mg (71%) of 26 as a white solid.

Workup

  1. filtrationPd (c) was filtered
  2. customthe solvent removed via a rotary evaporator
  3. customThe residue was purified by chromatography on silica gel using 7:3 hexane/ethyl acetate as the eluent

Sources & evidence

ORD record
ord-83d195fcb6b9425d9266ebe84f447879
Source dataset
uspto-grants-2010_04
Patent number
US07700616B2

Reaction notes

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