Formic Acid → HCID 86627512, compound

HRID 1969987Notes

Reaction equation

HRID 1969987 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][C:12]1[CH:21]=[CH:20][C:19]2[NH:18][C:17](=[O:22])[C:16]3[NH:23][CH:24]=[CH:25][C:15]=3[C:14]=2[CH:13]=1.Cl.[CH2:27]([C:29]([OH:31])=[O:30])[CH3:28].C(N(CC)CC)C>CN(C)C=O>[CH:1]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[NH:18][C:17](=[O:22])[C:16]3[NH:23][CH:24]=[CH:25][C:15]=3[C:14]=2[CH:13]=1)=[O:2].[CH2:27]([C:29]([O-:31])=[O:30])[CH3:28]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68937404HCID 68937404, compound

Product 1

HCID 86627512HCID 86627512, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

74 μL (1.95 mmol) of formic acid is added slowly to 153 μL (1.63 mmol) of acetic anhydride cooled on an ice bath, then the reaction mixture is stirred for 2 hours at 60° C. The mixture is cooled to room temperature then added to a solution of 500 mg (1.63 mmol) of 8-amino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate hydrochloride (synthesis 64) dissolved in 5 mL of anhydrous dimethylformamide and 460 μL (3.25 mmol) of triethylamine. The reaction mixture is stirred for 2 hours at 60° C. The solvent is evaporated and the residue is triturated in hot methanol to give 359 mg (74%) of 8-formylamino-4-oxo-4,5-dihydro-3H -pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a pale pink solid.

Workup

  1. temperaturecooled on an ice bath
  2. temperatureThe mixture is cooled to room temperature
  3. stirringThe reaction mixture is stirred for 2 hours at 60° C
  4. customThe solvent is evaporated
  5. customthe residue is triturated in hot methanol

Sources & evidence

ORD record
ord-5f843267eaaf40eb99f93d2d1975cf74
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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