Phenol → HCID 12593746, compound

HRID 1448488Notes

Reaction equation

HRID 1448488 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=[C:4]2[C:12]([CH3:16])([CH3:15])[O:13][CH2:14][C:3]=12.C1(O)C=CC=CC=1.[CH3:24][N:25]([CH2:27][CH2:28][NH2:29])[CH3:26]>CCOCC>[CH3:24][N:25]([CH3:26])[CH2:27][CH2:28][NH:29][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=[C:4]2[C:12]([CH3:16])([CH3:15])[O:13][CH2:14][C:3]=12

Participants

5

Reactant 3

HCID 996PhenolHCID 66053N,N-DimethylethylenediamineHCID 12593745HCID 12593745, compound

Product 1

HCID 12593746HCID 12593746, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of the starting material of formula I, 9-chloro-1,3-dihydro-3,3-dimethylfuro[3,4-b]quinoline (8.0 g, described in Example 31), phenol (15g) and the amine of formula H--Y--X, dimethylaminoethylamine (9.8 g), is heated at 150° C. for 18 hours under an atmosphere of nitrogen. Ether is added and the reaction is washed with 10% sodium hydroxide solution. The organic phase is extracted with 6 N hydrochloric acid and the aqueous phase is washed with ether. The aqueous phase is basified with 10% sodium hydroxide and extracted with ether. The organic extract is washed with water, dried, evaporated and crystallized from ethyl acetate to yield the title compound, mp 126°-127° C. The corresponding hydrochloride salt of the title compound is crystallized from ethanol, mp 182°-190° C.

Workup

  1. washthe reaction is washed with 10% sodium hydroxide solution
  2. extractionThe organic phase is extracted with 6 N hydrochloric acid
  3. washthe aqueous phase is washed with ether
  4. extractionextracted with ether
  5. extractionThe organic extract
  6. washis washed with water
  7. customdried
  8. customevaporated
  9. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-74e9182db80444ec8a304597d1cfb392
Source dataset
uspto-grants-1979_12
Patent number
US04180580

Reaction notes

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