Hydrochloric Acid → Methyl 7-methoxy-2-methyl-1H-indole-3-carboxylate

HRID 480575Notes

Reaction equation

HRID 480575 reaction equation
N#N.[CH3:3][C:4]1[NH:5][C:6]2[C:11]([C:12]=1[C:13](=[O:18])C(Cl)(Cl)Cl)=[CH:10][CH:9]=[CH:8][C:7]=2[O:19][CH3:20].[OH-:21].[K+].Cl.[CH3:24]O>>[CH3:3][C:4]1[NH:5][C:6]2[C:11]([C:12]=1[C:13]([O:18][CH3:24])=[O:21])=[CH:10][CH:9]=[CH:8][C:7]=2[O:19][CH3:20]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 947NitrogenHCID 14797Potassium HydroxideHCID 187654172-Methyl-3-trichloroacetyl-7-methoxyindole

Product 1

HCID 18765423Methyl 7-methoxy-2-methyl-1H-indole-3-carboxylateYield 96%

Procedure

To a 1 L round-bottomed flask equipped with a magnetic stirrer and a N2 bubbler were added 2-methyl-3-trichloroacetyl-7-methoxyindole (22.8 g, 74.37 mmol) and MeOH (150 mL). The mixture was stirred at RT to give a slurry. KOH (42.5 wt %, 2 mL) was added and the reaction stirred for 5 min. HCl (0.1N, 500 mL) was added dropwise. The slurry was stirred at RT for 1 h and filtered. The cake was washed with DI water (3×30 mL) and suction dried for 18 h to give 2-methyl-3-methoxycarbonyl-7-methoxyindole (15.57 g, 96% yield). 1H NMR (CDCl3) δ2.71 (s, 3H), 3.89 (s, 3H), 3.92 (s, 3H), 6.63 (d, J=7.9 Hz, 1H), 7.12 (dd, J=7.9, 8.0 Hz, 1H), 7.66 (d, J=8.0 Hz, 1H), 8.84 (s, 1H).

Workup

  1. customTo a 1 L round-bottomed flask equipped with a magnetic stirrer
  2. customto give a slurry
  3. stirringthe reaction stirred for 5 min
  4. stirringThe slurry was stirred at RT for 1 h
  5. filtrationfiltered
  6. washThe cake was washed with DI water (3×30 mL) and suction
  7. customdried for 18 h

Sources & evidence

ORD record
ord-9fc84f33682449c3b6c199c69d68d8ce
Source dataset
uspto-grants-2003_11
Patent number
US06653304B2

Reaction notes

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