Hydroxylamine → HCID 42606653, compound

HRID 1186685Notes

Reaction equation

HRID 1186685 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[C:7]([CH:12]=1)[C:8](OC)=[O:9].[NH2:18][OH:19].O.[OH-].[K+]>C1COCC1.C(Cl)Cl.CO>[OH:19][NH:18][C:8](=[O:9])[C:7]1[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 962WaterHCID 14797Potassium HydroxideHCID 66863626HCID 66863626, compound

Product 1

HCID 42606653HCID 42606653, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of methyl 5-methoxy-2-(thiophen-2-yl)benzoate 10 (0.13 g, 0.524 mmol) and a solution of 50% hydroxylamine in water (0.53 mL, 0.524 mmol) in THF (1 mL) and MeOH (1 mL) was added KOH (0.117 g, 2.094 mmol) and the reaction mixture was allowed to stir at room temperature for 3 hours. The reaction mixture was solvent evaporated, diluted with DCM, washed with 5% KHSO4, brine, dried over MgSO4, filtered and solvent evaporated to provide title compound 11 (50 mg, 38% yield) as a white solid after trituration (overnight, DCM). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.87 (s, 1H), 9.06 (s, 1H), 7.49 (d, J=1.2 Hz, 1H), 7.45 (dd, J=15.5, 1.2 Hz, 1H), 7.14 (dd, J=3.5, 1.2 Hz, 1H), 7.05 to 7.02 (m, 2H), 6.84 (d, J=2.7 Hz, 1H), 3.78 (s, 3H). LRMS (ESI): (calc.) 249.05 (found) 250.1 (MH)+

Workup

  1. customevaporated
  2. additiondiluted with DCM
  3. washwashed with 5% KHSO4, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customsolvent evaporated

Sources & evidence

ORD record
ord-24c70a8cc91c4f5db1f5226cad8a768b
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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