Hydrochloric Acid → HCID 68525961, compound

HRID 1932462Notes

Reaction equation

HRID 1932462 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=2[O:22][CH3:23])=[N:6][CH:7]=1.N1C=CC=CC=1.[Cl:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][C:39]=1[Cl:40])[C:34](Cl)=[O:35].Cl>ClCCl>[Cl:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][C:39]=1[Cl:40])[C:34]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=2[O:22][CH3:23])=[N:6][CH:7]=1)=[O:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 68527029HCID 68527029, compound

Product 1

HCID 68525961HCID 68525961, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice cooling, to a solution of ethyl 3-(4-(5-aminopyridin-2-yloxy)-3-methoxyphenyl)propionate (1.43 g, 4.5 mmol) in dichloromethane (30 mL) was added pyridine (0.44 mL, 5.4 mmol), and then 3,4-dichlorobenzoyl chloride (0.99 g, 4.7 mmol). The resulting solution was stirred for 1 hour under ice cooling, and then for 10 hours at room temperature. To the resulting reaction solution was added 10% hydrochloric acid, and extracted with dichloromethane. The dichloromethane layer was washed with water, dried over anhydrous magnesium sulfate, and evaporated. To the residue was added diethyl ether, and stirred. The precipitates were collected by filtration. After washing with water and diethyl ether, the precipitates were air dried at 60° C., to thereby yield 0.52 g of the title compound.

Workup

  1. waitfor 10 hours at room temperature
  2. customTo the resulting reaction solution
  3. extractionextracted with dichloromethane
  4. washThe dichloromethane layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. additionTo the residue was added diethyl ether
  8. stirringstirred
  9. filtrationThe precipitates were collected by filtration
  10. washAfter washing with water and diethyl ether
  11. customdried at 60° C.

Sources & evidence

ORD record
ord-d0bbf179ea2c478b914ddbe07bb1aed4
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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