M-Cresol → m-Cresyl 3-indolylglyoxylate

HRID 461389

Reaction equation

HRID 461389 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:14])[C:11](Cl)=[O:12])=[CH:2]1.[CH:15]1[C:20]([OH:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:22].N1C=CC=CC=1>C(OCC)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:14])[C:11]([O:21][C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:22])[CH:15]=2)=[O:12])=[CH:2]1

Participants

5

Reactant 3

HCID 342M-CresolHCID 1049PyridineHCID 899523-Indoleglyoxylyl chloride

Product 1

HCID 21393607m-Cresyl 3-indolylglyoxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Indolylglyoxylyl chloride (104 g. ) was stirred in diethyl ether (500 ml.) and treated with m-cresol (108 g.) followed by pyridine (79 g.). After stirring for 30 minutes the solid product was collected by filtration, washed with water then with acetonitrile and dried to give m-cresyl 3-indolylglyoxylate as a yellow powder, m.p. 194°-197°. Yield 119 g. (85.5%)

Workup

  1. filtrationwas collected by filtration
  2. washwashed with water
  3. dry with materialwith acetonitrile and dried

Sources & evidence

ORD record
ord-934fc004b6e84a2bb6c09c3080607a5b
Source dataset
uspto-grants-1977_12
Patent number
US04062869

Linked notes

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