4-Iodoaniline → N-(4-iodophenyl)-7-methyl-3H-imidazo[4,5-f]quinolin-9-amine;hydrochloride

HRID 268249Notes

Reaction equation

HRID 268249 reaction equation
[ClH:1].[NH:2]([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)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[I:23]C1C=CC(N)=CC=1>C(O)C>[ClH:1].[I:23][C:6]1[CH:7]=[CH:8][C:3]([NH:2][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]4[N:21]=[CH:20][NH:19][C:17]4=3)[N:12]=[C:11]([CH3:22])[CH:10]=2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 108934-IodoanilineHCID 178428198HCID 178428198, compound

Product 1

HCID 178428218N-(4-iodophenyl)-7-methyl-3H-imidazo[4,5-f]quinolin-9-amine;hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 500 ml., 3-neck, r.b. flask fitted with stirrer, condenser and thermometer was charged with the compound of Example I, C. (24.8 g., 0.114 mole), 4-iodoaniline (25 g., 0.114 mole) and ethanol (300 ml.). The mixture was stirred and heated overnight. The mixture was concentrated to dryness by rotary evaporator and the residue was collected and dried at 100°C to yield 49 g. (97.7%) brown crystals, m.p. 296°-305°C. Recrystallization from ethanol gave m.p. 313°-315°C.

Workup

  1. customflask fitted with stirrer, condenser
  2. temperatureheated overnight
  3. concentrationThe mixture was concentrated to dryness by rotary evaporator
  4. customthe residue was collected
  5. customdried at 100°C
  6. customto yield 49 g
  7. customRecrystallization from ethanol
  8. customgave m.p. 313°-315°C.

Sources & evidence

ORD record
ord-12c648a8ff584417a7e3fe373de59384
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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