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Hydrochloric Acid → HCID 68525961, compound

HRID 884110
Notes
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Reaction equation

HRID 884110 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344Dichloromethane
Solvent

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-15002a5bcdad469db0d6cf2a8f39fb2b
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08236826B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes