Hydroxylamine → 2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)-N-hydroxyacetamide

HRID 20638Notes

Reaction equation

HRID 20638 reaction equation
[NH2:1][OH:2].[CH:3]1([O:8][C:9]2[C:10]([O:27][CH3:28])=[CH:11][CH:12]=[C:13]3[C:18]=2[O:17][C:16](=[O:19])[CH:15]=[C:14]3[NH:20][CH2:21][C:22](OCC)=[O:23])[CH2:7][CH2:6][CH2:5][CH2:4]1>C(O)C>[CH:3]1([O:8][C:9]2[C:10]([O:27][CH3:28])=[CH:11][CH:12]=[C:13]3[C:18]=2[O:17][C:16](=[O:19])[CH:15]=[C:14]3[NH:20][CH2:21][C:22]([NH:1][OH:2])=[O:23])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 24849429ethyl 2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)acetate

Product 1

HCID 248494312-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)-N-hydroxyacetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine (0.5 mL, 50% water, 8.2 mmol) was added to a solution of ethyl 2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)acetate (40 mg, 0.11 mmol, Example 8) and ethanol (0.5 mL) and stirred vigorously. After 6 h, the precipitate was filtered, washed with 65% ethanol (2 mL), and dried to give 2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)-N-hydroxyacetamide: 1H NMR (400 MHz, DMSO-d6): δ 10.77 (s, 1H), 8.97 (s, 1H), 7.93 (t, 1H), 7.71 (d, 1H), 7.07 (d, 1H), 4.90 (s, 1H), 4.80 (m, 1H), 3.86 (s, 3H), 3.77 (d, 2H), 1.90-1.46 (m, 8H); MS (ESI): 348.9.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with 65% ethanol (2 mL)
  3. customdried

Sources & evidence

ORD record
ord-77f48e61d0a843d4b83d54808275e3f7
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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