Methanol → HCID 18946729, compound

HRID 248922Notes

Reaction equation

HRID 248922 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH2:5]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:18]([O:20][CH3:21])=[O:19])[CH2:6][CH2:7][CH3:8].[CH3:22][OH:23].O>C1(C)C=CC=CC=1.ClCCl>[CH2:5]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[C:22]([O:2][CH3:1])=[O:23])=[CH:15][CH:14]=[CH:13][C:12]=2[C:18]([O:20][CH3:21])=[O:19])[CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6371PhosgeneHCID 18946596HCID 18946596, compound

Product 1

HCID 18946729HCID 18946729, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of phosgene in toluene (37 ml, 1.9M) was added to a solution of methyl 2-(n-butyl)indole-7-carboxylate (P) 11.5 g) (prepared, e.g., as described in Preparation 10), at 5° C. in dichloromethane (75 ml). The solution was stirred at room temperature for 16 hours, cooled in an ice bath, and treated with methanol (20 ml). Water was added, and the dichloromethane layer was separated and solvent evaporated under reduced pressure. Chromatography on silica gel, eluting with 20% ethyl acetate/hexane, afforded dimethyl 2-(n-butyl)indole-3,7-dicarboxylate (7.4 g), a compound of Formula (Q), as an oil.

Workup

  1. custom(prepared, e.g., as described in Preparation 10)
  2. customat 5° C.
  3. temperaturecooled in an ice bath
  4. customthe dichloromethane layer was separated
  5. customsolvent evaporated under reduced pressure
  6. washChromatography on silica gel, eluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b85ec6f1dd6e40d080cb71f7e976eb67
Source dataset
uspto-grants-1993_05
Patent number
US05212195

Reaction notes

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