Pyridine → HCID 86591959, compound

HRID 489254Notes

Reaction equation

HRID 489254 reaction equation
[CH2:1](N/[C:9](/[CH3:17])=[C:10](/[CH3:16])\[C:11]([O:13]CC)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:18]1C=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH3:24][O:25]CC(Cl)=O.C([O:32]CC)C>>[CH2:21]([CH2:20][C:19]([NH:18][O:25][CH2:24][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:32])[CH3:22].[CH3:16]/[C:10](=[CH:9]\[CH3:17])/[C:11]([O-:13])=[O:12]

Participants

5

Reactant 4

HCID 1049PyridineHCID 3283Diethyl Ether2×HCID 96623Methoxyacetyl chlorideHCID 15716741HCID 15716741, compound

Product 1

HCID 86591959HCID 86591959, compoundYield 91.3%

Procedure

Ethyl 3-benzylamino-2-methylcrotonate (1-004-02) (97.83 g) was dissolved in diethyl ether (2 L). The reaction mixture was stirred under ice-cooling and nitrogen atmosphere. After pyridine (35.6 mL) was added to the reaction mixture, a solution of methoxyacetyl chloride (40.2 mL) in diethyl ether was added dropwise to the reaction mixture at 5 to 6° C. as internal temperature for 45 min. After 2 h, the reaction mixture was poured into ice-water (1.5 L), extracted twice with diethyl ether, and washed with water (1 L) and an aqueous solution of sodium bicarbonate. The extract was dried over magnesium sulfate, and evaporated under reduced pressure to give ethyl 1-benzylmethoxyacetamide-2-methylcrotonate (1-004-03) (111.47 g, 91.3%) as an oil.

Workup

  1. temperaturecooling
  2. extractionextracted twice with diethyl ether
  3. washwashed with water (1 L)
  4. dry with materialThe extract was dried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ba6c215f3f894f62a501de0619ad6725
Source dataset
uspto-grants-2005_12
Patent number
US06977266B2

Reaction notes

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