Hydroxylamine → Methyl 2-(hydroxycarbamoyl)benzo[b]thiophene-6-carboxylate

HRID 545469Notes

Reaction equation

HRID 545469 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=[CH:13][C:7]=2[CH:6]=1)=O.[NH2:18][OH:19]>CC(N(C)C)=O.CO>[CH3:17][O:16][C:14]([C:11]1[CH:12]=[CH:13][C:7]2[CH:6]=[C:5]([C:3](=[O:2])[NH:18][OH:19])[S:9][C:8]=2[CH:10]=1)=[O:15]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 59556411Dimethyl benzo[b]thiophene-2,6-dicarboxylate

Product 1

HCID 44440676Methyl 2-(hydroxycarbamoyl)benzo[b]thiophene-6-carboxylate

Reagents, catalysts & solvents 1

HCID 17933507HCID 17933507, compoundSolvent

Procedure

To a solution of benzo[b]thiophene-2,6-dicarboxylic acid dimethyl ester (115 mg, 0.46 mmol) in DMA/MeOH (3/1 mL) NH2OH (50% aq., 1.5 mL). The solution was stilted until the disappearance of starting material as indicated by LC/MS. After removal of solvent, MeOH/H2O was added until a precipitate forms. The solid was filtered yielding the desired material. 1H NMR (DMSO-d6) δ 11.57 (br s, 1H), 9.36 (br s, 1H), 8.67 (s, 1H), 8.05-7.87 (m, 3H), 3.87 (s, 3H). MS (EI): cal'd (MH+) 252.07, exp (MH+), 252.20.

Workup

  1. customAfter removal of solvent, MeOH/H2O
  2. additionwas added until a precipitate forms
  3. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-bd5e6af5431047b798016efe5e77ba72
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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