3-Bromo-4-chloroquinoline → HCID 14209243, compound

HRID 2165844Notes

Reaction equation

HRID 2165844 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1Cl)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl.[NH2:14][CH2:15][C:16]1([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(OC(O)C)C>C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:14][CH2:15][C:16]1([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 6183063-Bromo-4-chloroquinolineHCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)HCID 101298981-Ethoxyethanol

Product 1

HCID 14209243HCID 14209243, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-bromo-4-chloroquinoline (12.1 g), 1-aminomethyl-1-cyclohexanol HCl (8.3 g), triethylamine (7.2 g) and 30 ml of ethoxyethanol was stirred at 120° C. for 5 hours and poured into 250 ml of ice water. The solid was filtered and recrystallized from acetone. The yield was 6.5 g, mp 130°-132° C.

Workup

  1. filtrationThe solid was filtered
  2. customrecrystallized from acetone

Sources & evidence

ORD record
ord-4f7b7501b804427d8838d00b4f6b6a89
Source dataset
uspto-grants-1990_07
Patent number
US04942168

Reaction notes

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