Hydrochloric Acid → HCID 19755371, compound

HRID 1588437Notes

Reaction equation

HRID 1588437 reaction equation
ClC1C=CC(C[N:7]2[C:19]3[CH:18]([CH2:20][C:21]([OH:23])=[O:22])[CH2:17][CH2:16][CH2:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[C:11]([O:27][CH2:28][C:29]2[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=2)[C:12]=3CC=C)=CC=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:48][C:49]1C=CC2C(=CC=CC=2)N=1.Cl>CN(C=O)C.O>[N:30]1[C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:37]=[CH:38][C:29]=1[CH2:28][O:27][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:19]1[CH:18]([CH2:20][C:21]([O:23][CH2:48][CH3:49])=[O:22])[CH2:17][CH2:16][CH2:15][C:14]2=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 19755406HCID 19755406, compound

Product 1

HCID 19755371HCID 19755371, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To the phenol ester of Example 9, Step 2 (8.86 g, 32.4 mmol) in anhydrous DMF (50 ml) was added K2CO3 (6.72 g, 48.6 mmol) followed by 2-(chloromethyl)quinoline (7.49 g, 42.1 mmol). The mixture was stirred for 48 hours at room temperature. 2N HCl was added carefully until neutral to litmus paper. H2O (300 ml) was added and the mixture was extracted with EtOAc (6×100 ml). The combined organic layers were washed with water (400 ml) and dried over MgSO4. Evaporation and flash chromatography (20% EtOAc in hexane) afforded ethyl 6-(quinolin-2-ylmethoxy)-1,2,3,4-tetrahydrocarbazol-1-ylacetate.

Workup

  1. extractionthe mixture was extracted with EtOAc (6×100 ml)
  2. washThe combined organic layers were washed with water (400 ml)
  3. dry with materialdried over MgSO4
  4. customEvaporation and flash chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-800285cb22ca41579ed484c6c5fe5128
Source dataset
uspto-grants-1993_06
Patent number
US05221678

Reaction notes

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