Hydrochloric Acid → HCID 59410101, compound

HRID 1805181Notes

Reaction equation

HRID 1805181 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[C:3]1[C:12]([NH:14][C:15]1[CH:16]=[C:17]([C:24]([O:26]CC)=[O:25])[C:18]2[CH:19]=[CH:20][NH:21][C:22]=2[CH:23]=1)=[O:13].[OH-].[Na+].Cl>O>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[C:3]1[C:12]([NH:14][C:15]1[CH:16]=[C:17]([C:24]([OH:26])=[O:25])[C:18]2[CH:19]=[CH:20][NH:21][C:22]=2[CH:23]=1)=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59410075HCID 59410075, compound

Product 1

HCID 59410101HCID 59410101, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 6-(4-oxo-1,4-dihydroquinoline-3-carboxamido)-1H-indole-4-carboxylate (6 mg, 0.02 mmol) was suspended in 1 M NaOH (400 μL, 0.40 mmol) and heated to 50° C. for 30 min. The clear brown solution was diluted with water (1 mL) and acidified with 1N HCl (450 uL). The solution was washed with water (3×1 mL), and purified via reverse phase HPLC (75% acetonitrile/water) to give 6-(4-oxo-1,4-dihydroquinoline-3-carboxamido)-1H-indole-4-carboxylic acid. LC/MS: m/z 347.8 (M+H)+ at 1.07 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Workup

  1. washThe solution was washed with water (3×1 mL)
  2. custompurified via reverse phase HPLC (75% acetonitrile/water)

Sources & evidence

ORD record
ord-1fc2bd142b1a4ab1ac3b2f3e102dbb4a
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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