Methanol → HCID 21949959, compound

HRID 2215813Notes

Reaction equation

HRID 2215813 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C:11](Cl)(=[O:15])[C:12](Cl)=[O:13].C(Cl)Cl.[CH3:20][O-:21].[Na+].CO>C(OCC)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11](=[O:15])[C:12]([O:21][CH3:20])=[O:13]

Participants

7

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 119785-MethylindoleHCID 65578Oxalyl chlorideHCID 10942334Sodium Methoxide

Product 1

HCID 21949959HCID 21949959, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-methyl-1H-indole (1.00 g, 7.6 mmol) in diethyl ether (10 mL) at 4° C. was added a 2.0 M solution of oxalyl chloride in methylene chloride (4.0 mL, 8.0 mmol). The resulting solution was allowed to warm to room temperature and stirred for 1.5 h. The solution was cooled to −78° C. To this solution was added 25% (w/w) solution of sodium methoxide in methanol (3.65 mL, 16.0 mmol). The resulting solution was allowed to warm to room temperature. After one hour, the solution was filtered to give the title compound (1.16 g, 70%) as a light brown solid. 1H NMR (DMSO-d6) δ 8.31 (m, 1H), 7.95 (s, 1H), 7.42 (m, 1H), 7.11 (m, 1H), 3.88 (s, 3H), 2.41 (s, 3H).

Workup

  1. temperatureThe solution was cooled to −78° C
  2. temperatureto warm to room temperature
  3. waitAfter one hour
  4. filtrationthe solution was filtered

Sources & evidence

ORD record
ord-24b946591eec4ec6a0606d1ea856ee7e
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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