Hydrochloric Acid → HCID 85357459, compound

HRID 1935482Notes

Reaction equation

HRID 1935482 reaction equation
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.[OH2:8].O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].Cl.[NH2:26]O.[O:28]([C:35]1[CH:36]=[C:37]([CH:39]=[CH:40][CH:41]=1)[NH2:38])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>O.CCO>[OH:8][N:26]=[CH:2][C:3]([NH:38][C:37]1[CH:39]=[CH:40][CH:41]=[C:35]([O:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:36]=1)=[O:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 62649Sodium sulfate decahydrateHCID 771353-PhenoxyanilineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 85357459HCID 85357459, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 1.0 g (6.0 mmol) of chloral hydrate in 25 mL of water was added 7.0 g (22 mmol) of sodium sulfate decahydrate, followed by a solution of 1.18 g (17.0 mmol) of hydroxylamine hydrochloride in 10 mL of water. A solution of 1.0 g (5.4 mmol) of 3-phenoxyaniline in 10 mL of1.0 N HCl was then added with stirring. The resulting suspension was warmed, and 40 mL of 95% EtOH was added to dissolve the suspenion. The solution was refluxed for 0.75 h and then cooled to ambient temperature. The resulting solid was collected by vacuum filtration and air dried to afford 0.95 g (67%) of 2-hydroxyimino-N-(3-phenoxyphenyl)acetamide as a solid: 1H NMR (DMSO-d6): δ 6.42 (d, J=8.4 Hz, 1H), 7.06 (d, J=7.9 Hz, 2H), 7.18 (t, J=7.3 Hz, 1H), 7.25-7.50 (m, 5H), 7.64 (s, 1H), 10.29 (s, 1H), 12.21 (s, 1H); APCI−MS: m/z 255 (M−H)−. A suspension of 0.15 g (0.58 mmol) of 2-hydroxyimino-N-(3-phenoxyphenyl)acetamide in 0.4 mL of BF3 etherate was heated to 85° C. for 0.75 h. The mixture was cooled to rt and 10 g of crushed ice was added. The resulting solid was collected by vacuum filtration and subjected to flash chromatography on silica gel (hexane/EtOAc 1.5:1) to afford 6-phenoxy-1H-indole-2,3-dione as a solid (0.018 g, 13%): 1H NMR (DMSO-d6): δ 6.44 (d, J=2.0 Hz, 1H), 6.56 (dd, J=2.0, 8.4 Hz, 1H), 7.08 (d, J=8.2 Hz, 1H), 7.22-7.29 (m, 1H), 7.38-7.46 (m, 2H), 7.52 (d, J=8.4 Hz, 1H), 9.05 (s, 1H); APCI−MS: m/z 255 (M+Na)+.

Workup

  1. temperatureThe resulting suspension was warmed
  2. dissolutionto dissolve the suspenion
  3. temperatureThe solution was refluxed for 0.75 h
  4. filtrationThe resulting solid was collected by vacuum filtration and air
  5. customdried

Sources & evidence

ORD record
ord-17b45f56c0644391bcabdff43ff00e97
Source dataset
uspto-grants-2002_05
Patent number
US06387919B1

Reaction notes

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