Nitric Acid → 2-chloro-5-nitro-1H-indole-3-carbaldehyde

HRID 1957213Notes

Reaction equation

HRID 1957213 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.C(OC(=O)C)(=O)C.[N+:20]([O-])([OH:22])=[O:21]>C(O)(=O)C>[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][C:7]([N+:20]([O-:22])=[O:21])=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 7918Acetic AnhydrideHCID 3147912-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 38092012-chloro-5-nitro-1H-indole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

15 g of (1) was added to a mixture of 150 ml acetic acid and 150 ml of acetic anhydride at 0°. 3.5 ml of 100% HNO3 was slowly added, and after 1 hour another 3.5 ml of 100% HNO3 was added. Stirring was continued for 1 hour at 0° C. The mixture was then added to ice, left in the cold overnight, and filtered to give 10 g of (65), which was used without further purification.

Workup

  1. additionThe mixture was then added to ice
  2. waitleft in the cold overnight
  3. filtrationfiltered

Sources & evidence

ORD record
ord-028b6254660e4b0bbd903cb9211373aa
Source dataset
uspto-grants-1998_07
Patent number
US05783575

Reaction notes

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