Hydrochloric Acid → HCID 68940251, compound

HRID 1969986Notes

Reaction equation

HRID 1969986 reaction equation
[CH:1]([NH:3][C:4]1[CH:13]=[CH:12][C:11]2[NH:10][C:9](=[O:14])[C:8]3[NH:15][CH:16]=[CH:17][C:7]=3[C:6]=2[CH:5]=1)=O.[CH2:18]([C:20]([O-:22])=[O:21])[CH3:19].[ClH:23]>O1CCCC1.C(OCC)C>[CH3:1][NH:3][C:4]1[CH:13]=[CH:12][C:11]2[NH:10][C:9](=[O:14])[C:8]3[NH:15][CH:16]=[CH:17][C:7]=3[C:6]=2[CH:5]=1.[ClH:23].[CH2:18]([C:20]([OH:22])=[O:21])[CH3:19]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86627512HCID 86627512, compound

Product 1

HCID 68940251HCID 68940251, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

0.41 mL (0.41 mmol) of a 1M solution of a borane-tetrahydrofuran complex in tetrahydrofuran is added to a solution of 45 mg (0.15 mmol) of 8-formylamino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 0.5 mL of anhydrous tetrahydrofuran. The reaction mixture is stirred overnight at room temperature then for 8 hours under reflux before further addition of 0.3 mL of a 1M solution of a borane-tetrahydrofuran complex in tetrahydrofuran. The reaction mixture is then stirred for 3 hours under reflux. The solvent is evaporated under reduced pressure, and the residue is taken up in 1 mL of anhydrous ethanol and 0.76 mL (1.52 mmol) of 2M hydrochloric acid in diethyl ether. The solution is stirred at 70° C. for 3 hours. The precipitate is filtered, washed with ethanol then with diethyl ether to give 24 mg (50%) of 8-methylamino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate hydrochloride in the form of a white solid.

Workup

  1. stirringThe reaction mixture is then stirred for 3 hours
  2. temperatureunder reflux
  3. customThe solvent is evaporated under reduced pressure
  4. stirringThe solution is stirred at 70° C. for 3 hours
  5. filtrationThe precipitate is filtered
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-c8e5ad5d3cc745bea535e6941a552de1
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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