Hydrochloric Acid → HCID 25253303, compound

HRID 604361Notes

Reaction equation

HRID 604361 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][N:13]=[CH:14][CH:15]=3)[C:10]3[CH:17]=[CH:18][C:19]([C:21]([O:23]C)=[O:22])=[CH:20][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCO.[OH-].[Na+].Cl>O>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][N:13]=[CH:14][CH:15]=3)[C:10]3[CH:17]=[CH:18][C:19]([C:21]([OH:23])=[O:22])=[CH:20][C:9]=3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 25253301HCID 25253301, compound

Product 1

HCID 25253303HCID 25253303, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

methyl 5-phenylbenzo[c][2,6]naphthyridine-8-carboxylate (147 mg, 0.468 mmol) was reacted with EtOH (3 ml) and 6 N NaOH (1 ml) at 60° C. for 2 hours. Water was added and the mixture acidified using 6N HCl. The solid was filtered and washed with water. The material was triturated in AcOEt/hexanes, filtered and dried to afford 5-phenylbenzo[c][2,6]naphthyridine-8-carboxylic acid as an off-white solid (121 mg, 86% yield). LCMS (ES): >95% pure, m/z 301[M+1]+.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water
  3. customThe material was triturated in AcOEt/hexanes
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-acee8fe31c6e4254ba81dd7f17851c83
Source dataset
uspto-grants-2011_03
Patent number
US07910600B2

Reaction notes

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