Chlorosuccinimide → Ethyl 8-amino-7-chloro-2,3-dihydro-1,4-benzodioxine-5-carboxylate

HRID 1067274Notes

Reaction equation

HRID 1067274 reaction equation
[NH2:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.[Cl:17]N1C(=O)CCC1=O>O1CCOCC1.O>[NH2:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][C:3]=1[Cl:17]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 15817382Ethyl 8-amino-2,3-dihydro-1,4-benzodioxine-5-carboxylate

Product 1

HCID 15817383Ethyl 8-amino-7-chloro-2,3-dihydro-1,4-benzodioxine-5-carboxylateYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

37 g (0.165 mol) of ethyl 8-amino-2,3-dihydro-1,4-benzodioxine-5-carboxylate dissolved in 370 ml of dioxane are introduced into a 1 l round-bottomed flask, 23.2 g (0.174 mol) of N-chlorosuccinimide are added, at room temperature and with magnetic stirring, and the mixture is stirred overnight. It is diluted with water, extracted with ethyl acetate and, after the usual processing of the organic phase, 42 g of compound are obtained, which product is recrystallized from a mixture of diethyl ether and diisopropyl ether.

Workup

  1. additionare introduced into a 1 l round-bottomed flask
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-b0bd0cfe4d194ca19f4473507599a689
Source dataset
uspto-grants-2001_06
Patent number
US06248757B1

Reaction notes

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