Dichloromethane → HCID 21584326, compound

HRID 583276Notes

Reaction equation

HRID 583276 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-e828edf657ff413591e495015b64c675
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

Loading…