HCID 86627510, compound → HCID 86627509, compound

HRID 1969984Notes

Reaction equation

HRID 1969984 reaction equation
[N+:1]([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-])=O.[CH2:18]([C:20]([O-:22])=[O:21])[CH3:19]>C(O)(=O)C.[Fe]>[C:20]([NH:1][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:21])[CH3:18].[CH2:18]([C:20]([O-:22])=[O:21])[CH3:19]

Participants

4

Reactant 1

HCID 86627510HCID 86627510, compound

Product 1

HCID 86627509HCID 86627509, compoundYield 10.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

134 mg (2.4 mmol) of iron is added to 72 mg (0.24 mmol) of 8-nitro-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate (synthesis 66) dissolved in 4 mL of acetic acid. The mixture is refluxed for 1 h. The solution is filtered while hot and the solid is rinsed with a minimum of hot acetic acid. The filtrate is evaporated, then the residue (mixture of 8-acetylamino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate and 8-amino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate 85/15) is purified by preparative LCMS to give 4 mg (5%) of 8-acetylamino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a gray solid.

Workup

  1. temperatureThe mixture is refluxed for 1 h
  2. filtrationThe solution is filtered while hot and the solid
  3. washis rinsed with a minimum of hot acetic acid
  4. customThe filtrate is evaporated
  5. additionthe residue (mixture of 8-acetylamino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate and 8-amino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate 85/15)
  6. customis purified by preparative LCMS

Sources & evidence

ORD record
ord-c6deaaccf89a41f4bec5e5d157753c93
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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