Chlorosuccinimide → HCID 22168222, compound

HRID 1031597Notes

Reaction equation

HRID 1031597 reaction equation
[ClH:1].[NH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[O:8][C:9]([C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10].[Cl:18]N1C(=O)CCC1=O>CN(C=O)C>[ClH:18].[NH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[O:8][C:9]([C:11]2[C:16]([C:17]=1[Cl:1])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 221682233-(3-Aminopropoxy)-1H-2-benzopyran-1-one--hydrogen chloride (1/1)

Product 1

HCID 22168222HCID 22168222, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.13 g of 3-(3-aminopropoxy)isocoumarin hydrochloride (0.5 mmole) was chlorinated with 0.007 g of N-chlorosuccinimide (0.5 mmole) in 5 ml of DMF at r.t. overnight. The reaction mixture was purified by silica gel column chromatography (methylene chloride:methanol=5:1) and crystallized from MeOH-ether to give 0.009 g of 3-(3-aminopropoxy)-4-chloro-isocoumarin hydrochloride (yield, 60%). The NMR spectrum of this compound is similar to 3-(3-aminopropoxy)isocoumarin without the peak at δ6.2 ppm; m.p. 160°-163° C.; mass spectrum, m/e=254 (M+ -Cl). Anal. Calc. for C12H13N1O3Cl2.1/4H2O: C, 48.88; H, 4.61; N, 4.75; Cl, 24.06. Found: C, 48.85; H, 4.54; N, 4.74; Cl, 24.02.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (methylene chloride:methanol=5:1)
  2. customcrystallized from MeOH-ether

Sources & evidence

ORD record
ord-be44b0b6a5704e338e32a6c2a241c432
Source dataset
uspto-grants-1990_09
Patent number
US04954519

Reaction notes

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