Ammonium Hydroxide → HCID 19761401, compound

HRID 373832Notes

Reaction equation

HRID 373832 reaction equation
C1(N[N:8]=[C:9]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[NH2:19])[CH3:10])C=CC=CC=1.[NH4+].[OH-]>O>[NH2:19][C:12]1[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=1[C:9]1[NH:8][C:11]2[C:16]([CH:10]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86746352HCID 86746352, compound

Product 1

HCID 19761401HCID 19761401, compoundYield 164.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To polyphosphoric acid (30 ml) preheated to 110° C. was added 1.95 g 1-(2-amino-5-methoxyphenyl)ethanone phenylhydrazone in small portions under N2. The reaction was maintained at 110°-120° C. for forty-five minutes. This mixture was poured directly into excess water and made basic with concentrated NH4OH. Extraction with dichloromethane, drying (MgSO4) and concentration yielded 1.5 g 2-(2-amino-5-methoxyphenyl)-1H-indole as a solid, m.p. 97°-99° C.

Workup

  1. custompreheated to 110° C.
  2. temperatureThe reaction was maintained at 110°-120° C. for forty-five minutes
  3. extractionExtraction with dichloromethane
  4. customdrying
  5. concentration(MgSO4) and concentration

Sources & evidence

ORD record
ord-eb28910226d044c485ed60614c62c914
Source dataset
uspto-grants-1992_11
Patent number
US05166170

Reaction notes

Loading…