Phenol → 11-Phenoxy-1,2,4,5-tetrahydro-3-azepino[4,5-b]quinoline-carboxylic acid ethyl ester

HRID 1288187Notes

Reaction equation

HRID 1288187 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:20][CH2:19][C:18]2[C:9](=[N:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:17]=2Cl)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:20][CH2:19][C:18]2[C:9](=[N:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:17]=2[O:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 996PhenolHCID 2150364411-chloro-3-ethoxycarbonyl-1,2,4,5-tetrahydro-3H-azepino[4,5-b]quinoline

Product 1

HCID 5423109711-Phenoxy-1,2,4,5-tetrahydro-3-azepino[4,5-b]quinoline-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 15.0 gm (49.4 millimols) of 11-chloro-1,2,4,5-tetrahydro-3-azepino[4,5-b]quinoline-carboxylic acid ethyl ester and 28.2 gm (300 millimols) of phenol was melted at 150° C and held at that temperature for 40 hours. Then, the mixture was taken up in ethyl acetate, and the solution was extracted with dilute sodium hydroxide. The ethyl acetate phases were evaporated and chromatographed on a silicagel column with toluene/acetone (8:1) as the eluant. Subsequently, the crystals were triturated with ether/petroleum ether.

Workup

  1. extractionthe solution was extracted with dilute sodium hydroxide
  2. customThe ethyl acetate phases were evaporated
  3. customchromatographed on a silicagel column with toluene/acetone (8:1) as the eluant
  4. customSubsequently, the crystals were triturated with ether/petroleum ether

Sources & evidence

ORD record
ord-dfe7b2acd7bb4ce0995ab0bb82a780ae
Source dataset
uspto-grants-1976_10
Patent number
US03987047

Reaction notes

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