Dichloromethane → HCID 54210183, compound

HRID 583279Notes

Reaction equation

HRID 583279 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([N+:15]([O-:17])=[O:16])=[CH:11][CH:12]=2)[CH2:7][NH:6]1)=[O:4].ClCCl.[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(N(CC)CC)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([N+:15]([O-:17])=[O:16])=[CH:11][CH:12]=2)[CH:7]([C:23](=[O:24])[CH2:22][Cl:21])[NH:6]1)=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 53635299HCID 53635299, compound

Product 1

HCID 54210183HCID 54210183, compoundYield 105.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 7-nitro-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid methyl ester (Example 33(a), 4.466 g, 18.9 mmol), dichloromethane (130 ml) and triethylamine (3.0 ml), cooled in an ice bath, was added dropwise chloroacetyl chloride (1.74 ml, 21.8 mmol). The resulting reaction mixture was stirred for 2 h at room temperature. The reaction mixture was then 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-chloroacetyl-7-nitro-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid methyl ester (6.22 g).

Workup

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

Sources & evidence

ORD record
ord-45055c5d78e5471ea5f58893a516e1d1
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

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