Acetic Anhydride → HCID 18318073, compound

HRID 1700276Notes

Reaction equation

HRID 1700276 reaction equation
[CH3:1][C:2]1([CH3:15])[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][CH3:14])[CH:8]=2)[NH:3]1.ClC(C)(C#C)C.[C:22](OC(=O)C)(=[O:24])[CH3:23]>>[C:22]([N:3]1[C:4]2[C:9](=[CH:8][C:7]([O:12][CH2:13][CH3:14])=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]1([CH3:15])[CH3:1])(=[O:24])[CH3:23]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 706791-Butyne, 3-chloro-3-methyl-HCID 18318065HCID 18318065, compound

Product 1

HCID 18318073HCID 18318073, compound

Conditions

Temperature
100 °C

Procedure

A solution of 30.2 mmol (6.15 g) of 2,2-dimethyl-6-ethoxy-1,2-dihydroquinoline (prepared according to the procedure described in Steps 1 and 2 of Example 1 starting from 2-chloro-2-methyl-3-butyne) in 45 ml of acetic anhydride is heated at 100° C. under an inert atmosphere for 3 hours. After cooling, the medium is concentrated and the residue is purified by chromatography on silica gel, using a dichloromethane:ethyl acetate mixture 95:5 as eluant, to yield the expected compound.

Workup

  1. temperatureAfter cooling
  2. concentrationthe medium is concentrated
  3. customthe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-827e1bdb30dd402d93b7f2613794475b
Source dataset
uspto-grants-2002_02
Patent number
US06350759B1

Reaction notes

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