Dichloromethane → HCID 21584326, compound

HRID 369976Notes

Reaction equation

HRID 369976 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH:9]([CH2:14][OH:15])[NH:10][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].ClCCl.[Cl:19][CH2:20][C:21](Cl)=[O:22]>C(N(CC)CC)C>[Cl:19][CH2:20][C:21]([N:10]1[CH:9]([CH2:14][OH:15])[CH2:8][C:7]2[C:12](=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:11]1)=[O:22]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 21584368191041-29-9

Product 1

HCID 21584326HCID 21584326, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 7-nitro-1,2,3,4-tetrahydroisoquinoline-3-methanol (1.648 g, 7.92 mmol), dichloromethane (60 ml) and triethylamine (1.1 ml), cooled in an ice bath, was added chloroacetyl chloride (0.651 ml). The resulting solution was stirred overnight at room temperature. The reaction mixture was washed with dilute hydrochloric acid and then with water. The organic phase was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to yield 2-chloro-1-(3-hydroxymethyl-7-nitro-1,2,3,4-tetrahydroisoquinolin-2-yl)ethanone (2.08 g); MS 285 (M+H)+.

Workup

  1. temperaturecooled in an ice bath
  2. washThe reaction mixture was washed with dilute hydrochloric acid
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1b05d8c800854c8bbe2601ea239dde99
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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