Hydrochloric Acid → HCID 14986954, compound

HRID 2248095Notes

Reaction equation

HRID 2248095 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl>O.C(OCC)C>[CH3:16][C:13]([CH3:17])([N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[C:2]1[CH2:11][C:10]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:14][OH:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14986943HCID 14986943, compound

Product 1

HCID 14986954HCID 14986954, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 26.7 g (0.115 mole) of 2-[(3-amino-4-quinolinyl)amino]-2,2-dimethyl-1-ethanol and 42.8 g (0.180 mole) of triethyl orthophenylacetate was heated at 130° C. for four hours. The mixture was diluted with water, acidified to pH 5 with 6N hydrochloric acid and diluted with diethyl ether. The solid which precipitated was separated by filtration, rinsed with diethyl ether and slurried in saturated sodium bicarbonate solution. The solid was separated by filtration and dried to provide beta,beta-dimethyl-2-phenylmethyl-1H-imidazo[4,5-c]quinoline-1-ethanol. The structural assignment was confirmed by nuclear magnetic resonance spectral analysis.

Workup

  1. customThe solid which precipitated
  2. customwas separated by filtration
  3. washrinsed with diethyl ether
  4. customThe solid was separated by filtration
  5. customdried

Sources & evidence

ORD record
ord-d3168f9babc348d5bd2792339ec49bba
Source dataset
uspto-grants-1991_08
Patent number
US05037986

Reaction notes

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