Ammonia → HCID 15222812, compound

HRID 260055Notes

Reaction equation

HRID 260055 reaction equation
Cl[C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:22]>CO>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[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]([NH2:22])[C:11]=2[N:12]=[CH:13]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19704390HCID 19704390, compound

Product 1

HCID 15222812HCID 15222812, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2.4 g of 4-chloro-1-(2-pyridylmethyl)-1H-imidazo[4,5-c]quinoline and 50 mL of 15% ammonia in methanol was placed in a bomb and heated at 150° C. for 6 hours. After cooling, the reaction mixture was filtered. The solid was slurried with aqueous sodium bicarbonate, collected and dried to provide 1.9 g of crude product. The crude product was recrystallized from 350 mL of ethanol to provide 1.25 g of a solid, m.p. 278°-284° C. The mother liquor was concentrated to a volume of 50 mL to provide a second crop of 0.32 g, m.p. 275°-281° C. The two crops were combined for analysis. Analysis: Calculated for C16H13N5 : % C, 69.8; % H, 4.8; % N, 25.4; Found % C, 69.7; % H, 4.8; % N, 25.2.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. customcollected
  4. customdried
  5. customto provide 1.9 g of crude product
  6. customThe crude product was recrystallized from 350 mL of ethanol

Sources & evidence

ORD record
ord-4efd6d89d75240fa97be54dc16d97c14
Source dataset
uspto-grants-1996_06
Patent number
US05525612

Reaction notes

Loading…