Chlorosuccinimide → HCID 178516336, compound

HRID 639017Notes

Reaction equation

HRID 639017 reaction equation
[O:1]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[O:4][CH2:3][CH2:2]1)[NH:11][CH:10]=[CH:9][C:8]3=[O:15].[Cl:16]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:16][C:9]1[CH:10]=[N:11][C:12]2[C:7]([C:8]=1[OH:15])=[C:6]1[O:1][CH2:2][CH2:3][O:4][C:5]1=[CH:14][CH:13]=2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 21873753HCID 21873753, compound

Product 1

HCID 178516336HCID 178516336, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
35 °C

Procedure

2,3-Dihydro-7H-[1,4]dioxino[2,3-f]quinolin-10-one (6.93 g, 34.1 mmol, 1 eq) in acetic acid (95.9 mL) was sonicated and warmed until all had dissolved, and then it was treated with N-chlorosuccinimide (5.01 g, 37.5 mmol, 1.1 eq) and the mixture was heated at 35° C. for 18 hr, cooled and the solid collected and washed with acetic acid and dried in vacuo at 40 oC overnight, to give a white solid (5.93 g, 73%). LC/MS (ES) m/z 237 (MH+ 84%); 1H-NMR (400 MHz, d6-DMSO), 8.17 (1H, d, J=6.28, CHNHC), 7.21 (1H, d, J=8.96 Hz, CHCO), 7.01 (1H, d, J=9, CHCN), 4.29-4.25 (4H, m, 2×(CH2O)).

Workup

  1. temperaturewarmed until
  2. dissolutionall had dissolved
  3. temperaturecooled
  4. customthe solid collected
  5. washwashed with acetic acid
  6. customdried in vacuo at 40 oC overnight

Sources & evidence

ORD record
ord-9404555542ce42ee884f58a1d1b0809a
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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