Hydrochloric Acid → 2-formyl-1H-indole-3-carbonitrile

HRID 2097100Notes

Reaction equation

HRID 2097100 reaction equation
Cl.C(OC(OCC)[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]#[N:16])=[C:7]1[CH:17]=[O:18])C.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH:17]([C:7]1[NH:6][C:14]2[C:9]([C:8]=1[C:15]#[N:16])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 592776141-diethoxymethyl-2-formyl-1H-indole-3-carbonitrile

Product 1

HCID 592775632-formyl-1H-indole-3-carbonitrileYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Hydrochloric acid (4 mL, 20%) was added to a THF (100 mL) solution of 1-diethoxymethyl-2-formyl-1H-indole-3-carbonitrile (5.33 g, 19.57 mmol) at 0° C. The mixture was stirred at 20° C. for 41 h then treated with 5% aqueous K2CO3 (25 mL). The reaction mixture was concentrated to 50 mL and treated with methylene chloride (200 mL). The organic layer was washed with water, dried and evaporated to afford the title compound (2.81 g, 84%). 1H NMR (300 MHz, DMSO-d6, δ): 13.20 (s, br, 1H), 10.02 (s, 1H), 7.82 (d, J=8.0 Hz, 1H), 7.63 (d, J=7.7 Hz, 1H), 7.51 (t, J=7.1 Hz, 1H), 7.37 (t, J=7.5 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated to 50 mL
  2. additiontreated with methylene chloride (200 mL)
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-4a47460586bb4ca99254f411992ea733
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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