Triethylamine → HCID 18403563, compound

HRID 1017572Notes

Reaction equation

HRID 1017572 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])C>ClCCl>[CH3:14][N:16]1[C:19]2[C:20](=[CH:5][CH:4]=[CH:9][CH:8]=2)[C:18]([C:10]2[C:11](=[O:12])[O:12][C:11](=[O:13])[C:10]=2[C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:17]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 158763-Nitrophenylacetic acid

Product 1

HCID 18403563HCID 18403563, compoundYield 110.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-methylindole-3-glyoxylyl chloride in dichloromethane (350 mL) was added to a solution of 3-nitrophenylacetic acid (8.5 g, 0.093 mL) and triethylamine (13 mL, 93 mmol) in dichloromethane (350 mL) at 0° C. The reaction mixture was then stirred at room temperature overnight and then concentrate under reduced pressure. The crude product was purified on a silica gel column with 6:1 hexane/ethyl acetate to afford 3-(1-methylindol-3-yl)-4-(3-nitrophenyl)furan-2,5-dione (9 g, 55%).

Workup

  1. concentrationconcentrate under reduced pressure
  2. customThe crude product was purified on a silica gel column with 6:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-2a17f77205514bdca1740953432a0f19
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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