Acetyl chloride → HCID 18963901, compound

HRID 257056Notes

Reaction equation

HRID 257056 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH2:22][CH2:23][NH:24][OH:25])[CH:17]=3)[C:12]2=[O:26])=[CH:4][CH:3]=1.[C:27](Cl)(=[O:29])[CH3:28].[O:31]1CC[CH2:33][CH2:32]1>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH2:22][CH2:23][N:24]([O:25][C:32](=[O:31])[CH3:33])[C:27](=[O:29])[CH3:28])[CH:17]=3)[C:12]2=[O:26])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 15227739HCID 15227739, compound

Product 1

HCID 18963901HCID 18963901, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[3-(4-fluorophenyl)-propyl]-6-[2-(N-hydroxyamino)-ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline (900 mg) in 25 ml of tetrahydrofuran is cooled to 0°. Acetyl chloride (0.50 g) is slowly added and the mixture is stirred for one hour at 0°. The mixture is then diluted with ethyl acetate and washed with aqueous 2N HCl, dried (MgSO4) and evaporated to give 2-[3-(4-fluorophenyl)-propyl]-6-[2-(N-acetyloxy-N-acetylamino)ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. washwashed with aqueous 2N HCl
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-0531e262635a4dae9587d55c2c89c523
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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