Ammonia → HCID 13982904, compound

HRID 1789442Notes

Reaction equation

HRID 1789442 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:25].C[OH:27]>>[OH2:27].[CH2:15]([N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:25])[C:11]=2[N:12]=[C:13]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:16]([CH3:18])[CH3:17]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 20188211HCID 20188211, compound

Product 1

HCID 13982904HCID 13982904, compound

Procedure

A mixture of 5.6 g (0.016 mole) of 4-chloro-1-isobutyl-2-phenyl-1H-imidazo[4,5-c]quinoline and 30 ml of a 20% mixture of ammonia in methanol was placed in a metal bomb and heated at 145°-150° C. for about 6 hours. After cooling, the solid was separated by filtration, washed with methanol and dried to provide 3.8 g of crude product. Recrystallization of the solid from ethanol provided 2.4 g of colorless 1-isobutyl-2-phenyl-1H-imidazo[4,5-c]quinolin-4-amine hydrate, melting point 194°-205° C. Analysis: Calculated for C20H20N4.1/2H2O: % C, 73.8; % H, 6.5: % N, 17.2. Found: % C, 73.6; % H, 6.2: % N, 17.0

Workup

  1. temperatureheated at 145°-150° C. for about 6 hours
  2. temperatureAfter cooling
  3. customthe solid was separated by filtration
  4. washwashed with methanol
  5. customdried
  6. customto provide 3.8 g of crude product
  7. customRecrystallization of the solid from ethanol

Sources & evidence

ORD record
ord-ccd81c7a01fc41eea9e96fd7b3fd7c67
Source dataset
uspto-grants-1987_08
Patent number
US04689338

Reaction notes

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