Hydroxyamine hydrochloride → HCID 72309684, compound

HRID 1253636Notes

Reaction equation

HRID 1253636 reaction equation
[CH3:1][C:2]1([CH3:16])[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[C:4](=O)[CH2:3]1.Cl.[NH2:18][OH:19].C([O-])(=O)C.[Na+]>CO>[OH:19][N:18]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:6]=2)[C:2]([CH3:16])([CH3:1])[CH2:3]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 19034437HCID 19034437, compound

Product 1

HCID 72309684HCID 72309684, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 1,1-dimethyl-3-oxo-2,3-dihydro-1H-indene-5-carboxylate (430 mg, 1.97 mmol, 1.0 eq.) in methanol (7.5 ml) was added hydroxylamine hydrochloride (340 mg, 4.93 mmol, 2.5 eq.) followed by sodium acetate (807 mg, 9.85 mmol, 5.0 eq.) and the reaction mixture was heated at reflux for 2 h at 80° C. The reaction mixture was concentrated and then extracted with ethyl acetate (3×40 ml). The organic part was separated, washed with water (20 ml) and brine (20 ml) and dried over sodium sulfate. After concentrating the filtrate the crude product thus obtained was directly taken through to the next step without purification.

Workup

  1. temperaturethe reaction mixture was heated
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate (3×40 ml)
  4. customThe organic part was separated
  5. washwashed with water (20 ml) and brine (20 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationAfter concentrating the filtrate the crude product
  8. customthus obtained
  9. customwas directly taken through to the next step without purification

Sources & evidence

ORD record
ord-be0f6c918bbd4c1fbca86d51ef9db668
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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