Pyridine → 3-Chloro-3-(2-ethoxy-phenyl)-5-methoxy-1,3-dihydro-indol-2-one

HRID 601775Notes

Reaction equation

HRID 601775 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1(O)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[NH:12][C:11]1=[O:21])[CH3:2].N1C=CC=CC=1.O=S(Cl)[Cl:31]>C(Cl)Cl>[Cl:31][C:10]1([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH2:1][CH3:2])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[NH:12][C:11]1=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 575177763-(2-Ethoxy-phenyl)-3-hydroxy-5-methoxy-1,3-dihydro-indol-2-one

Product 1

HCID 575177773-Chloro-3-(2-ethoxy-phenyl)-5-methoxy-1,3-dihydro-indol-2-oneYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5 g (16.7 mmol) of the intermediate from step A and 2.6 g (33.4 mmol) pyridine were dissolved in 50 mL CH2Cl2 and at 0° C. 3 g (25.1 mmol) SOCl2 were added slowly. Then the reaction mixture was stirred for 30 min. at 0° C. The reaction mixture was poured into an ice/water mixture and the organic phase was separated, washed with H2O, dried over magnesium sulfate and finally the solvent was removed in vacuo. The resulting residue was suspended in ether. The solid residue was separated and dried to give 3.2 g of the intermediate, which was used without further purification.

Workup

  1. customthe organic phase was separated
  2. washwashed with H2O
  3. dry with materialdried over magnesium sulfate
  4. customfinally the solvent was removed in vacuo
  5. customThe solid residue was separated
  6. customdried

Sources & evidence

ORD record
ord-b7fa2e0b05274412a217d0ccf39f38d6
Source dataset
uspto-grants-2011_03
Patent number
US07902379B2

Reaction notes

Loading…