Hydrochloric Acid → HCID 12593755, compound

HRID 2420115Notes

Reaction equation

HRID 2420115 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]2[NH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14](=[O:15])[C:5]=2[CH2:4][O:3]1.[H-].[Na+].[CH3:19][N:20]([CH2:22][CH2:23]Cl)[CH3:21].Cl>O1CCCC1>[CH3:1][C:2]1([CH3:16])[C:6]2=[N:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]([O:15][CH2:23][CH2:22][N:20]([CH3:21])[CH3:19])=[C:5]2[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 12593744HCID 12593744, compound

Product 1

HCID 12593755HCID 12593755, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the compound of formula VI, 3,4-dihydro-3,3-dimethylfuro[3,4-b]quinolin-9(1H)-one (8.0 g, described in Example 8), in tetrahydrofuran (80 ml) is slowly added over one hour to a suspension of 55% sodium hydride (4 g) in tetrahydrofuran (80 ml) at 20° to 30° C. The mixture is stirred at room temperature for one hour and dimethylaminoethyl chloride (prepared from 20 g of the hydrochloride) is added. The mixture is heated at reflux for 18 hours, filtered and the filtrate is evaporated. The residue is crystallized from acetonitrile to give the title compound, mp 92°-93° C. Treatment of the title compound with a solution of hydrogen chloride in ether gives the hydrochloride salt of the title compound, mp 165°-167° C.

Workup

  1. additionis added
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 18 hours
  4. filtrationfiltered
  5. customthe filtrate is evaporated
  6. customThe residue is crystallized from acetonitrile

Sources & evidence

ORD record
ord-c842e2345f174f85bd2ca0824bcaf758
Source dataset
uspto-grants-1978_08
Patent number
US04108998

Reaction notes

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