Water → HCID 131717043, compound

HRID 610358Notes

Reaction equation

HRID 610358 reaction equation
[O:1]([C@H:8]1[C@H:14]([OH:15])[C:13]2[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=1.O>CN(C)C=O>[O:1]([C@H:8]1[C@@H:14]([OH:15])[C:13]2[CH:16]=[C:17]([O:20][CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=3)[CH:18]=[CH:19][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 203942-(Chloromethyl)quinolineHCID 24758Sodium hydrideHCID 67592062HCID 67592062, compound

Product 1

HCID 131717043HCID 131717043, compoundYield 13.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 950 mg of the cis-title product of Example 29 in 25 ml of dimethylformamide was added 173 mg of 50% sodium hydride. After stirring for 20 minutes, 641 mg of 2-chloromethylquinoline was added. The reaction was stirred at room temperature for 1 hour, poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and evaporated in vacuo to afford the crude product which was purified by recrystallization from methyl acetate/hexane to afford 200 mg of title product, m.p. 130-132° C.

Workup

  1. stirringThe reaction was stirred at room temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  4. customevaporated in vacuo
  5. customto afford the crude product which
  6. customwas purified by recrystallization from methyl acetate/hexane

Sources & evidence

ORD record
ord-840884d6439e48b0a5db095f6e8deb81
Source dataset
uspto-grants-1999_12
Patent number
US05998451

Reaction notes

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