3-Bromo-7-chloro-N-(1-hydroxycyclohexylmethyl)-4-quinolinamine → 8'-Chloro-spiro[cyclohexane-1,3'-[3H][1,4]oxazino[2,3-c]quinoline]

HRID 2165854Notes

Reaction equation

HRID 2165854 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[CH:9][CH:8]=[C:7]([Cl:21])[CH:6]=2.CC(C)([O-])C.[K+]>CN(C)C=O>[Cl:21][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]=[CH:13][C:14]4([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]4)[O:20][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 142092443-Bromo-7-chloro-N-(1-hydroxycyclohexylmethyl)-4-quinolinamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 230425638'-Chloro-spiro[cyclohexane-1,3'-[3H][1,4]oxazino[2,3-c]quinoline]Yield 31.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 16.4 g of 3-bromo-7-chloro-N-[1-hydroxycyclohexylmethyl]-4-quinolinamine in 176 ml of dimethylformamide was stirred at room temperature and to it was added 7.54 g of potassium tert-butoxide. The mixture was heated at 130°-140° C. for twenty hours. The reaction mixture was then cooled to room temperature, quenched with water, and extracted with an ether/ethyl acetate solution. Evaporation of solvents resulted in a crude oil which was purified by HPLC using 2:1 hexane/ethyl acetate as the eluent. A solid resulted which was recrystallized from isopropanol to yield 4 g of crystalline solid with a melting point of 216°-218° C.

Workup

  1. temperatureThe mixture was heated at 130°-140° C. for twenty hours
  2. customquenched with water
  3. extractionextracted with an ether/ethyl acetate solution
  4. customEvaporation of solvents
  5. customresulted in a crude oil which
  6. customwas purified by HPLC
  7. customA solid resulted which
  8. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-3a6bd627a0914c6196d924531ddcaa7c
Source dataset
uspto-grants-1990_07
Patent number
US04942168

Reaction notes

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