Hydrochloric Acid → 2-Hydroxyimino-N-indan-5-yl-acetamide
Reaction equation
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.S([O-])([O-])(=O)=O.[Na+].[Na+].S(O)(O)(=O)=O.[NH2:20][OH:21].[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][CH2:27][CH2:26]2.Cl>O>[OH:21][N:20]=[CH:2][C:3]([NH:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][CH2:27][CH2:26]2)=[O:5]Participants
7
Conditions
- Temperature
- 45 °C
Procedure
To a solution of chloral hydrate (5.56 g, 33.63 mmol) and anhydrous sodium sulfate (28.58 g, 201.20 mmol) in water (90 mL) add a mixture of hydroxylamine sulfate (25.63 g, 156.16 mmol), 5-aminoindane (4 g, 30.03 mmol), concentrated hydrochloric acid (3.14 mL) in water (30 mL). Heat the mixture at 45° C. for 1 h and at 75° C. for 2 h. Cool the mixture to room temperature and filter the solid. Wash the solid with water and ethyl ether. Dry the solid under vacuum to yield the title compound (4.98 g, 81%). 1H NMR (dimethyl sulfoxide-d6, 300 MHz) δ 1.90 (quintuplet, J=7.8 Hz, 2H), 2.72 (q, J=7.8 Hz, 4H), 7.06 (d, J=8.2 Hz, 1H), 7.28 (dd, J=1.5, 8.2 Hz, 1H), 7.49 (bs, 1H), 9.94 (s, 1H), 12.02 (s, 1H). MS (ES−): 203 (M−H).
Workup
- temperatureCool the mixture to room temperature
- filtrationfilter the solid
- washWash the solid with water and ethyl ether
- customDry the solid under vacuum
Sources & evidence
- ORD record
- ord-083b841f56a146f5b6cd477152c8a551
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07786108B2
Reaction notes
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