Hydrochloric Acid → HCID 21460738, compound

HRID 2396378Notes

Reaction equation

HRID 2396378 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:12])=[CH:8][C:9]=2[Cl:11])[NH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19].Cl.N1C=CC=C[CH:32]=1>>[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](=[O:26])[CH2:32][NH:1][C:2]2[C:10]3[C:5](=[CH:6][C:7]([Cl:12])=[CH:8][C:9]=3[Cl:11])[NH:4][C:3]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 15043966HCID 15043966, compound

Product 1

HCID 21460738HCID 21460738, compoundYield 100%

Procedure

Dissolve 3-amino-2-carbethoxy-4,6-dichloroindole (10 g, 36.6 mmol) in anhydrous pyridine (100 mL). Add 4-nitrobenzoyl chloride (7.47 g, 40.27 mmol) and stir for 5 hours. Pour into 1N hydrochloric acid (500 mL) and extract into ethyl acetate. Evaporate the solvent in vacuo and dry at 70° C. under vacuum to give the title compound (15.75 g, 100%); mp 283°-86° C.

Workup

  1. extractionextract into ethyl acetate
  2. customEvaporate the solvent in vacuo
  3. customdry at 70° C. under vacuum

Sources & evidence

ORD record
ord-64af41921b6b4446aa7db0e788dcfb1d
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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