Hydrochloric Acid → Methyl indole-3-acetate

HRID 1983995Notes

Reaction equation

HRID 1983995 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([OH:13])=[O:12])=[CH:2]1.[CH3:14]O.Cl>C(OCC)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 802Indole-3-Acetic AcidHCID 887Methanol

Product 1

HCID 74706Methyl indole-3-acetateYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of commercially available (1H-indol-3-yl)acetic acid (200 g, 1.14 mol), methanol (2700 mL) and a saturated solution of HCl in diethyl ether (750 mL) was stirred at room temperature for 16 h. The solvent was removed in vacuo, and the residue was subjected to aqueous work-up under alkaline conditions by the use of aqueous ammonia to yield methyl (1H-indol-3-yl)acetate as an oil (202.5 g, 94%). The crude oil was dissolved in acetic acid (2 L), and sodium cyanoborohydride (60 g, 0.95 mol) was added in portions of 1 g over a period of 8 h. The resulting mixture was stirred at room temperature for 16 h and then poured onto an ice/water mixture. Aqueous work-up under alkaline conditions gave the crude product that was purified by flash chromatography (ethyl acetate/heptane 1:1) to give the title compound (97.3 g, 48%).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8ee9c7a61ec04663af33e5d032f726bc
Source dataset
uspto-grants-2009_06
Patent number
US07544685B2

Reaction notes

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