Iodoethane → HCID 24771191, compound

HRID 1162180Notes

Reaction equation

HRID 1162180 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:11][C:10]2[N:9]=[C:8]([CH3:12])[C:7]3[NH:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:6]=3[C:5]=2[C:4](=[O:20])[CH2:3]1.[H-].[Na+].I[CH2:25][CH3:26]>CN(C)C=O.O.[Cl-].[Na+].O>[CH2:25]([N:13]1[C:7]2[C:8]([CH3:12])=[N:9][C:10]3[CH2:11][C:2]([CH3:21])([CH3:1])[CH2:3][C:4](=[O:20])[C:5]=3[C:6]=2[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]1=2)[CH3:26]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 53324323,3,6-trimethyl-2,3,4,7-tetrahydroindolo[2,3-c]quinolin-1-one

Product 1

HCID 24771191HCID 24771191, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 3,3,6-trimethyl-2,3,4,7-tetrahydroindolo[2,3-c]quinolin-1-one of Example 4 (0.28 g, 1 mmol) in anhydrous N,N-dimethylformamide (4 mL) was added dropwise at room temperature under stirring to a suspension of sodium hydride (60% dispersion in mineral oil, 0.051 g, 1.3 mmol) in anhydrous N,N-dimethylformamide (4 mL). The reaction mixture was stirred for 2 h at room temperature, and then 1-iodoethane (0.19 g, 1.2 mmol) was added dropwise. The mixture was stirred at room temperature until the reaction was completed (4 h, thin layer chromatography control). The reaction mixture was diluted with water (25 mL) and brine (10 mL), and then extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over anhydrous sodium sulfate, and ethyl acetate was distilled off in vacuum to give the crude product (0.18 g, 60%). Crystallization from hexanes yielded the pure product as light orange crystals; m.p. 174-177° C.

Workup

  1. stirringThe mixture was stirred at room temperature until the reaction
  2. custom(4 h, thin layer chromatography control)
  3. extractionextracted with ethyl acetate (3×15 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate, and ethyl acetate
  5. distillationwas distilled off in vacuum
  6. customto give the crude product (0.18 g, 60%)
  7. customCrystallization from hexanes

Sources & evidence

ORD record
ord-16887bbcb29d4e94b9374f4092469c71
Source dataset
uspto-grants-2010_10
Patent number
US07820691B2

Reaction notes

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