Water → 2-Ethyl-1H-indole-3-carbaldehyde

HRID 1360990Notes

Reaction equation

HRID 1360990 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:2].P(Cl)(Cl)(Cl)=O.O.[OH-].[Na+].CN([CH:23]=[O:24])C>>[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[CH:23]=[O:24])=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:2]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 38016182-ethyl-1H-indole2×

Product 1

HCID 133838882-Ethyl-1H-indole-3-carbaldehyde

Conditions

Temperature
40 °C

Procedure

2-Ethylindole (0.5 g, 3.4 mmol) dissolved in DMF (2 mL) was added to a cold (0° C.) premixed (30 minutes) mixture of DMF (1.15 mL) and phosphorous oxychloride (0.64 g, 4.16 mmol). After addition of 2-ethylindole, the mixture was heated to 40° C. for 1 h, water (5 mL) was added and the pH adjusted to 5 by means of 1 N sodium hydroxide. The mixture was subsequently extracted with diethyl ether, the organic phase isolated, dried with MgSO4 and evaporated to dryness affording 2-ethylindole-3-carbaldehyde (300 mg).

Workup

  1. additionwas added to a cold (0° C.)
  2. additionpremixed
  3. extractionThe mixture was subsequently extracted with diethyl ether
  4. customthe organic phase isolated
  5. dry with materialdried with MgSO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-493b1a1751d6421e89af03fe91c94624
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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