Hydroxyamine hydrochloride → HCID 76689531, compound

HRID 1516989Notes

Reaction equation

HRID 1516989 reaction equation
[CH3:1][C:2]1[N:3]([CH2:12][C:13]([OH:15])=[O:14])[C:4]2[CH2:5][CH2:6][CH2:7][C:8](=O)[C:9]=2[CH:10]=1.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>C(O)C>[OH:18][N:17]=[C:8]1[CH2:7][CH2:6][CH2:5][C:4]2[N:3]([CH2:12][C:13]([OH:15])=[O:14])[C:2]([CH3:1])=[CH:10][C:9]1=2

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 581603442-(2-Methyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-1-YL)acetic acid

Product 1

HCID 76689531HCID 76689531, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(2-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl)acetic acid (4.0 g, 19 mmol), hydroxylamine hydrochloride (2.0 g, 29 mmol) and anhydrous sodium acetate (2.4 g, 29 mmol) in ethanol (40 mL) was heated under reflux for 6 h with stirring. After cooling to r.t. and holding overnight, the mixture was further cooled to 4° C. The solid product was collected by filtration, washed with water (15 mL) followed by ethanol (15 mL) then dried under vacuum at 40° C. to afford the title compound as a pale brown solid; 3.68 g (86%); purity: 96.7 area % by HPLC; m/z: 223 (MH+); 1H-NMR: 9.82 (1H, br s), 6.48 (1H, d, J=0.90 Hz), 4.58 (2H, s), 2.56-2.51 (2H, m), 2.29-2.24 (2H, m), 2.09 (3H, s), 1.86-1.79 (2H, m).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 h
  3. temperaturethe mixture was further cooled to 4° C
  4. filtrationThe solid product was collected by filtration
  5. washwashed with water (15 mL)
  6. customthen dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-2f275a8d05f540e28c7d8fc3937fdb8e
Source dataset
uspto-grants-2012_07
Patent number
US08227622B2

Reaction notes

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