Hydrochloric Acid → HCID 86672695, compound

HRID 2369854Notes

Reaction equation

HRID 2369854 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:14]([O:16][CH3:17])=[O:15])[CH:7]=[CH:6]1.Cl>C1COCC1>[O:2]=[CH:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:14]([O:16][CH3:17])=[O:15])[CH:7]=[CH:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66898716HCID 66898716, compound

Product 1

HCID 86672695HCID 86672695, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 1-(2,2-dimethoxyethyl)-1H-indole-7-carboxylate (1.8 g, 6.7 mmol) from Step A above in THF (30 ml) was added 1N HCl (30 ml). The mixture was heated to 60° C. for 2 h. The solvent was evaporated and the residue purified by column chromatography (silica gel, 70:30 hexanes/ethyl acetate) to afford methyl 1-(2-oxoethyl)-1H-indole-7-carboxylate (1.3 g, 87%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ 9.77 (s, 1H), 7.84 (dd, J=4.5, 1.0 Hz, 2H), 7.15 (t, J=8.0 Hz, 1H), 7.04 (d, J=1.5 Hz, 1H), 6.67 (d, J=1.5 Hz, 1H), 3.90 (s, 3H), 2.05 (s, 2H); MS (ESI+) m/z 218 (M+H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography (silica gel, 70:30 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-57417128c0e74a17b210d47d2827e09a
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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