Indole → Methyl 3-indoleglyoxylate

HRID 1246937Notes

Reaction equation

HRID 1246937 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.[CH3:16][O-:17].[Na+].CO>C(OCC)C>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:1](=[O:5])[C:2]([O:17][CH3:16])=[O:3])=[CH:8]1

Participants

6

Reactant 4

HCID 798Indole2×HCID 887MethanolHCID 65578Oxalyl chlorideHCID 10942334Sodium Methoxide

Product 1

HCID 588944Methyl 3-indoleglyoxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Oxalyl chloride (1.50 mL; 17.2 mmol) was added dropwise to an ice cold solution of indole, A1, (2.00 g; 17.1 mmol) in anhydrous diethyl ether (20 mL). The resulting solution was allowed to stir on ice for 1 hour after which time a yellow slurry had formed. A freshly prepared solution of sodium methoxide in methanol (780 mg Na metal in 20 mL methanol; 34.1 mmol) was added, the reaction allowed to warm to room temperature and stirred for 1 hour. The reaction was quenched with the addition of water (30 mL) and the resulting orange solid isolated by fitration, washed with diethyl ether and recrystallised from methanol. Yield 2.94 g; 85%. mp 226–228° C. 1H NMR (500 MHz, DMSO-d6) 12.40 (br s, 1H), 8.17 (dd, J=1.5, 7.6 Hz, 1H), 7.55 (dd, J=1.5, 7.6 Hz, 1H), 7.29 (dt, j=1.5, 7.6 Hz, 1H), 7.26 (dt, J=1.5, 7.6 Hz, 1H), 3.89 (s, 3H).

Workup

  1. customhad formed
  2. stirringstirred for 1 hour
  3. customThe reaction was quenched with the addition of water (30 mL)
  4. customthe resulting orange solid isolated by fitration
  5. washwashed with diethyl ether
  6. customrecrystallised from methanol

Sources & evidence

ORD record
ord-2755251c2dd84eeaadc0526987d7afec
Source dataset
uspto-grants-2006_10
Patent number
US07129250B2

Reaction notes

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