3'-Aminoacetophenone → HCID 178466589, compound

HRID 268267Notes

Reaction equation

HRID 268267 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1)=[O:3].[ClH:11].[NH:12]([C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]3[N:31]=[CH:30][NH:29][C:27]3=2)[N:22]=[C:21]([CH3:32])[CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[OH2:3].[ClH:11].[C:2]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[NH:10][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]3[N:31]=[CH:30][NH:29][C:27]3=2)[N:22]=[C:21]([CH3:32])[CH:20]=1)(=[O:3])[CH3:1].[C:2]([C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[NH:12][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]3[N:31]=[CH:30][NH:29][C:27]3=2)[N:22]=[C:21]([CH3:32])[CH:20]=1)(=[O:3])[CH3:1].[ClH:11]

Participants

4

Reactant 2

HCID 74173'-AminoacetophenoneHCID 178428198HCID 178428198, compound

Product 1

HCID 178466589HCID 178466589, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 13.5 g. (0.1 m.) of 3-aminoacetophenone, 21.7 g. (0.1 m.) of the compound of Example I, C. and 500 ml. of ethanol was heated at reflux overnight with stirring. The solution was concentrated in vacuo to give 30 g. m.p. 156°-223°C. The crude product was recrystallized from 1000 ml. of MeOH, followed by concentration of the filtrate to the cloud point. The product was oven-dried (100°C) to yield 24 g. m.p. 225° -228°, completely 251°C.

Workup

  1. additionA mixture of 13.5 g
  2. temperatureat reflux overnight
  3. concentrationThe solution was concentrated in vacuo
  4. customto give 30 g
  5. customThe crude product was recrystallized from 1000 ml
  6. customThe product was oven-dried (100°C)
  7. customto yield 24 g
  8. customm.p. 225° -228°, completely 251°C.

Sources & evidence

ORD record
ord-a69066a586954ad8982db4fd21f9a734
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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