Hydrochloric Acid → HCID 12593755, compound

HRID 1448490Notes

Reaction equation

HRID 1448490 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-26140b68870f4a25a727c57699b91bd1
Source dataset
uspto-grants-1979_12
Patent number
US04180580

Reaction notes

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