4-Nitroaniline → HCID 3755607, compound

HRID 1437798Notes

Reaction equation

HRID 1437798 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](O)=[CH:5]1)(=O)C.[N+:14]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)([O-:16])=[O:15]>C(O)(=O)C>[N+:14]([C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[NH:4][CH:5]=2)=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 4397011H-Indol-3-ol, 1-acetyl-

Product 1

HCID 3755607HCID 3755607, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

More in particular, to a mixture of N-acetyl-3-hydroxyindole (a) (0.114 mol, 20 g) in acetic acid (150 ml), was added 4-nitroaniline (1.5 equiv., 0.171 mol, 23.65 g). The mixture was heated at reflux for 5 hours and cooled to room temperature. An orange precipitate was filtered off and washed with isopropanol and diisopropyl ether, affording intermediate b.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 hours
  3. filtrationAn orange precipitate was filtered off
  4. washwashed with isopropanol and diisopropyl ether

Sources & evidence

ORD record
ord-d55a01f6b5a24bdfbfa0656855a49905
Source dataset
uspto-grants-2009_11
Patent number
US07622581B2

Reaction notes

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