Sodium Hydroxide → HCID 86710342, compound

HRID 1398344Notes

Reaction equation

HRID 1398344 reaction equation
[F-].C([O:6][C:7]([NH:9][C:10]1[N:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[CH:18]=[N+:17]([CH3:20])[C:16]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:15]2=1)=[O:8])(C)(C)C.[OH-].[Na+].[O-:28][Mn](=O)(=O)=O.[K+]>C(Cl)Cl.O>[Cl:25][C:22]1[CH:23]=[CH:24][C:15]2[C:14]3[C:19](=[C:10]([NH:9][C:7](=[O:8])[OH:6])[N:11]=[CH:12][CH:13]=3)[C:18](=[O:28])[N:17]([CH3:20])[C:16]=2[CH:21]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 86710340HCID 86710340, compound

Product 1

HCID 86710342HCID 86710342, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 4-((tert-butoxycarbonyl)amino)-8-chloro-6-methylbenzo[c][2,7]naphthyridin-6-ium fluoride (0.35 g, 0.65 mmol) and NaOH (0.162 g, 4.06 mmol) in a mixture of DCM (10 mL) and water (10 mL) was added KMnO4 (0.642 g, 4.06 mmol) in portions at rt and the reaction was heated to 90° C. for 1 h. The solution was diluted with water (10 mL) and extracted with DCM (2×20 mL). The combined organic layers were washed with water 50 mL, dried over sodium sulfate, and concentrated under reduced pressure to yield (8-chloro-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-4-yl)carbamic acid (305 mg, 0.422 mmol, 65% yield) as a yellow solid, which carried on without further purification. LC/MS (ESI) m/e 304.1 [(M+H)+, calcd for C14H11ClN3O3 304.04]; LC/MS retention time (Method D): tR=1.01 min.

Workup

  1. extractionextracted with DCM (2×20 mL)
  2. washThe combined organic layers were washed with water 50 mL
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8846671c650c465f8d5dbea342a4d865
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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