4-Butylaniline → p-n-Butylanilino-7-methyl-1H-imidazo[4,5-f]quinoline Hydrochloride

HRID 268243Notes

Reaction equation

HRID 268243 reaction equation
[ClH:1].N([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]3[N:21]=[CH:20][NH:19][C:17]3=2)[N:12]=[C:11]([CH3:22])[CH:10]=1)C1C=CC=CC=1.[CH2:23]([C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1)[CH2:24][CH2:25][CH3:26]>C(O)C>[ClH:1].[CH2:23]([C:27]1[CH:28]=[CH:29][C:30]([NH:31][N:19]2[C:17]3=[C:18]4[C:13](=[CH:14][CH:15]=[C:16]3[N:21]=[CH:20]2)[N:12]=[C:11]([CH3:22])[CH:10]=[CH:9]4)=[CH:32][CH:33]=1)[CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 76944-ButylanilineHCID 178428198HCID 178428198, compound

Product 1

HCID 131710111p-n-Butylanilino-7-methyl-1H-imidazo[4,5-f]quinoline Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the compound of Example I, C. (21.7 g., 0.1 mole) and p-n-butylaniline (14.9 g., 0.1 mole) in ethanol (200 ml.) was stirred and refluxed overnight. The reaction solution was concentrated to dryness by rotary evaporator and the residue was collected and dried at 100°C to yield 36.5 g. (99.7%) yellow crystals, m.p. 296°-303°C. A small sample (5.0 g.) was recrystallized from nitromethane (750 ml.) and dried to yield 1.9 g. yellow crystals, m.p. 287°-302°C. A repeated recrystallization gave m.p. 303°-306°C.

Workup

  1. temperaturerefluxed overnight
  2. concentrationThe reaction solution was concentrated to dryness by rotary evaporator
  3. customthe residue was collected
  4. customdried at 100°C
  5. customto yield 36.5 g
  6. customA small sample (5.0 g.) was recrystallized from nitromethane (750 ml.)
  7. customdried
  8. customto yield 1.9 g
  9. customA repeated recrystallization
  10. customgave m.p. 303°-306°C.

Sources & evidence

ORD record
ord-bfce4b96cef842bbbba38ccdefe0739e
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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