Water → HCID 22282666, compound

HRID 1374814Notes

Reaction equation

HRID 1374814 reaction equation
P(Cl)(Cl)(Cl)=O.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]3[O:17][CH2:16][CH2:15][C:13]3=2)[CH:8]=[CH:7]1.[OH-].[Na+].O.CN(C)[C:23](=[O:25])[CH3:24]>>[C:23]([C:8]1[C:9]2[C:14](=[C:13]3[CH2:15][CH2:16][O:17][C:12]3=[CH:11][CH:10]=2)[NH:6][CH:7]=1)(=[O:25])[CH3:24]

Participants

6

Reactant 5

HCID 962WaterHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 31374Dimethylacetamide2×HCID 22282663HCID 22282663, compound

Product 1

HCID 22282666HCID 22282666, compoundYield 74%

Procedure

To stirred N,N-dimethylacetamide (2.1 mL) under Ar at 0° C. was added phosphorous oxychloride (1.0 mL, 10.7 mmol) dropwise over 10 min. The resultant pale yellow mixture was allowed to warm to ambient temperature, then a solution of 7,8-dihydrofuro[2,3-g]indole (800 mg, 5.0 mmol) in N,N-dimethylacetamide (1.5 mL) was added over 3 min and the mixture was stirred for 2 h. The resultant suspension was heated at 65° C. for 30 min, then cooled in an ice-water bath. Ice (10 g) was added portionwise to the stirred mixture followed by the cautious addition of 20% aqueous sodium hydroxide (10 mL), then water (15 mL). The resultant mixture was heated to reflux for 10 min then cooled to room temperature and diluted with ice-water (50 mL). The suspension was filtered-off and dried to give the crude product (870 mg, 86%) as a beige solid. Recrystallisation from hot ether (10 mL) afforded the product (746 mg, 74%) as a cream-coloured solid: m.p. 233–234.5° C.; NMR (400 MHz, DMSO-d6) δH 2.41 (3H, s), 3.32 (1H, 2H, t, J 8.5 Hz), 4.58 (2H, t, J 8.5 Hz), 6.69 (1H, d, J 8.5 Hz), 7.91 (1H, d, J 8.5 Hz), 8.18 (1H, d, J 3.0 Hz) and 11.76 (1H, br s).

Workup

  1. temperaturecooled in an ice-water bath
  2. temperatureto reflux for 10 min
  3. temperaturethen cooled to room temperature
  4. customdried
  5. customto give the crude product (870 mg, 86%) as a beige solid
  6. customRecrystallisation from hot ether (10 mL)

Sources & evidence

ORD record
ord-a4355f72dafb42418c0e8f4d31a300a2
Source dataset
uspto-grants-2007_01
Patent number
US07166613B2

Reaction notes

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