Indole → 5-Nitrofuroyl chloride

HRID 249163

Reaction equation

HRID 249163 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)(=O)C([Cl:15])=O.[Cl-].[Al+3].[Cl-].[Cl-].[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1>ClCCl>[N+:1]([C:4]1[O:8][C:7]([C:9]([Cl:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:1]([C:4]1[O:8][C:7]([C:9]([C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:22][CH:23]=2)=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 798IndoleHCID 125775-Nitro-2-Furoic AcidHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride

Product 2

HCID 907115-Nitrofuroyl chlorideHCID 19024851HCID 19024851, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 5-nitro-2-furoyl chloride, which was prepared with 5-nitro-2-furoic acid (2.0 g) and oxalyl chloride (1.4 ml) in an usual manner, in dichloromethane (10 ml) was added to a suspension at aluminum chloride (1.78 g) at 25° C. The mixture was stirred at 25° C. for 30 minutes, and then a solution of indole (1.49 g) in dichloromethane (15 ml) was added at 25° C. The mixture was stirred at 25° C. for 1 hour, and poured into ice water. The precipitates were filtered and washed with water, ethyl acetate and hot ethanol to give 3-(5-nitro-2-furoyl)indole (1.08 g) as yellow powder.

Workup

  1. stirringThe mixture was stirred at 25° C. for 1 hour
  2. filtrationThe precipitates were filtered
  3. washwashed with water, ethyl acetate and hot ethanol

Sources & evidence

ORD record
ord-505a9244395c4de98f5cf9f809946273
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Linked notes

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