Pyridine → HCID 178483597, compound

HRID 553691Notes

Reaction equation

HRID 553691 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[CH3:11].[CH3:12][O:13][C:14](=[O:20])[CH:15]=[C:16]([NH:18][CH3:19])[CH3:17].N1C=CC=CC=1.Cl.N1C=CC=CC=1>O1CCCC1>[CH3:12][O:13][C:14](=[O:20])[CH:15]([C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([CH3:11])[CH:4]=1)/[C:16](=[N:18]/[CH3:19])/[CH3:17]

Participants

6

Reactant 4

HCID 1049PyridineHCID 2734182Methyl 3-(methylamino)but-2-enoateHCID 70215344-Bromo-3-methylbenzoyl chlorideHCID 10176127Pyridinium chloride

Product 1

HCID 178483597HCID 178483597, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-bromo-3-methyl-benzoyl chloride (40.0 mmol) in tetrahydrofuran (300 mL) wad added 3-methylamino-but-2-enoic acid methyl ester (5.12 g, 40.0 mmol), followed by pyridine (3.2 mL, 40.0 mmol), and the reaction was stirred overnight at room temperature. Solid pyridine hydrochloride coated the flask, so the mixture was decanted, and the solid was washed three times with EtOAc. The combined solutions were concentrated and diluted with EtOAc (500 mL), and the mixture was washed three times with water. The aqueous layer was separated and back-extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customso the mixture was decanted
  2. washthe solid was washed three times with EtOAc
  3. concentrationThe combined solutions were concentrated
  4. additiondiluted with EtOAc (500 mL)
  5. washthe mixture was washed three times with water
  6. customThe aqueous layer was separated
  7. extractionback-extracted with EtOAc
  8. dry with materialthe combined organic layers were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-542c7c626e854bafb27f7d11d9fc2f8a
Source dataset
uspto-grants-2011_11
Patent number
US08048902B2

Reaction notes

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