Hydrochloric Acid → 5-Acetoxymethyl-7-nitro-1H-indole-2-carboxylic acid methyl ester

HRID 1045845Notes

Reaction equation

HRID 1045845 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6](C(OC(C)(C)C)=O)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH2:14][O:15][C:16](=[O:18])[CH3:17])=[CH:9][C:8]=2[N+:19]([O-:21])=[O:20])=[O:4].Cl>ClCCl>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH2:14][O:15][C:16](=[O:18])[CH3:17])=[CH:9][C:8]=2[N+:19]([O-:21])=[O:20])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 594480931-BOC-5-acetoxymethyl-7-nitro-indole-2-carboxylic acid methyl ester

Product 1

HCID 595429365-Acetoxymethyl-7-nitro-1H-indole-2-carboxylic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-BOC-5-acetoxymethyl-7-nitro-indole-2-carboxylic acid methyl ester (4.7 g, 12.0 mmol) prepared in Step A was dissolved in dichloromethane (50 mL). 2N hydrochloric acid solution (30 mL, 60 mmol) was added thereto, and the mixture was stirred for 12 h at room temperature. The reaction mixture was distilled under reduced pressure to give the solid title compound (3.5 g, Yield 100%).

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-75ef0b54dab04119b41f8203f07f4ac6
Source dataset
uspto-grants-2013_10
Patent number
US08569307B2

Reaction notes

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