Hydrochloric Acid → HCID 68937404, compound

HRID 1969988Notes

Reaction equation

HRID 1969988 reaction equation
C([O-])=O.[NH4+].[N+:5]([C:8]1[CH:17]=[CH:16][C:15]2[NH:14][C:13](=[O:18])[C:12]3[NH:19][CH:20]=[CH:21][C:11]=3[C:10]=2[CH:9]=1)([O-])=O.[CH2:22]([C:24]([O-:26])=[O:25])[CH3:23].[ClH:27]>[Pd].CN(C)C=O.C(OCC)(=O)C.C(OCC)C>[NH2:5][C:8]1[CH:17]=[CH:16][C:15]2[NH:14][C:13](=[O:18])[C:12]3[NH:19][CH:20]=[CH:21][C:11]=3[C:10]=2[CH:9]=1.[ClH:27].[CH2:22]([C:24]([OH:26])=[O:25])[CH3:23]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 2723923Ammonium formate2×HCID 86627510HCID 86627510, compound

Product 1

HCID 68937404HCID 68937404, compoundYield 92.6%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalyst2×HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

0.22 g of palladium on charcoal (10 wt. %) and 3.74 g (59.25 mmol) of ammonium formate are added to 3.57 g (11.65 mmol) of 8-nitro-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate (synthesis 66) suspended in 80 mL of anhydrous dimethylformamide. The reaction mixture is stirred overnight at 60° C. then 0.50 g of palladium on charcoal (10 wt. %) and 0.75 g (11.89 mmol) of ammonium formate are added. Stirring is continued for 4 h. The mixture is then diluted in ethyl acetate and filtered on celite. The filtrate is evaporated and triturated in ether to give, after filtration, 3.16 g of a mixture of 8-amino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate and 8-formylamino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate. The beige residue is suspended in 40 mL of anhydrous ethanol before adding 11.7 mL (23.29 mmol) of 2M hydrochloric acid in diethyl ether. The solution is stirred for 90 minutes then filtered to give 3.34 g (92%) of 8-amino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate hydrochloride in the form of a light violet solid.

Workup

  1. stirringStirring
  2. waitis continued for 4 h
  3. filtrationfiltered on celite
  4. customThe filtrate is evaporated
  5. customtriturated in ether
  6. customto give
  7. filtrationafter filtration, 3.16 g of a mixture of 8-amino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate and 8-formylamino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate
  8. stirringThe solution is stirred for 90 minutes
  9. filtrationthen filtered

Sources & evidence

ORD record
ord-ac7bbb10a2cb437fa1d3f1ee7d81dacb
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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