HCID 57271201, compound → HCID 20392021, compound

HRID 1863516Notes

Reaction equation

HRID 1863516 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH2:11][CH2:12][N:13](C(OCC(Cl)(Cl)Cl)=O)[CH2:14][CH:15]=1>C(O)(=O)C.O.[Zn]>[NH:13]1[CH2:14][CH:15]=[C:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 1

HCID 57271201HCID 57271201, compound

Product 1

HCID 20392021HCID 20392021, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 52.6 g of 4-(2-benzoxazolyl)-3,6-dihydro-1(2H)-pyridinecarboxylic acid, 2,2,2-trichloroethyl ester in 1250 ml of glacial acetic acid is gradually added 92.5 g of zinc dust and the reaction mixture stirred at room temperature under nitrogen for 6 hours. The reaction mixture is filtered and concentrated on the rotary evaporator to give a viscous gum. This material is suspended in 500 ml of water, the pH adjusted to 2-3, and the suspension extracted with 500 ml of ether in two portions. These are combined, dried and concentrated to give 11.32 g of unreacted starting material.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated on the rotary evaporator
  3. customto give a viscous gum
  4. extractionthe suspension extracted with 500 ml of ether in two portions
  5. customdried
  6. concentrationconcentrated
  7. customto give 11.32 g

Sources & evidence

ORD record
ord-86f3e10adf904811ac746144b2cb6762
Source dataset
uspto-grants-1979_09
Patent number
US04169200

Reaction notes

Loading…