Pyridine → HCID 20464813, compound

HRID 325310Notes

Reaction equation

HRID 325310 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[CH3:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]=1[NH:18][CH:19]1[CH2:24][O:23][C:21](=[O:22])[CH2:20]1.N1C=CC=CC=1>ClCCl>[CH3:1][O:2][CH2:3][C:4]([N:18]([CH:19]1[CH2:24][O:23][C:21](=[O:22])[CH2:20]1)[C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 13191334HCID 13191334, compound

Product 1

HCID 20464813HCID 20464813, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A 2.4 g (0.022 mol) sample of methoxyacetyl chloride was added dropwise to a solution of 5.5 g (0.022 mol) 3-(N-2-methylnaphth-1-ylamino)-gamma-butyrolactone and 1.7 g (0.022 mol) pyridine in 100 ml dichloromethane. The reaction mixture was stirred one hour at about 25° C. and then heated under reflux for 6 hours. After cooling overnight, the reaction mixture was washed successively with water, saturated sodium bicarbonate solution, water, dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed through a silica gel column. Elution with 25% acetone/75% petroleum ether gave 4.3 g of the product, m.p. 42°-46° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling overnight
  4. washthe reaction mixture was washed successively with water, saturated sodium bicarbonate solution, water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed through a silica gel column
  8. washElution with 25% acetone/75% petroleum ether

Sources & evidence

ORD record
ord-4cddc57f3d344207be0156996710d2da
Source dataset
uspto-grants-1984_04
Patent number
US04440780

Reaction notes

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