Water → HCID 178515238, compound

HRID 1471815Notes

Reaction equation

HRID 1471815 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10]C)=O)=[CH:6][N:5]=[C:4]2[NH:12][CH:13]=[CH:14][C:3]=12.[C:15]1([NH:21][NH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.[OH-].[Na+]>CO>[C:15]1([N:21]2[C:8](=[O:10])[C:7]3[C:2]([C:3]4[CH:14]=[CH:13][NH:12][C:4]=4[NH:5][CH:6]=3)=[N:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7516PhenylhydrazineHCID 14798Sodium HydroxideHCID 50989137HCID 50989137, compound

Product 1

HCID 178515238HCID 178515238, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 1 equivalent of compound 15 and 10 equivalents of phenyl hydrazine was heated to 90° C. for 16 hours. Water was added to the reaction mixture at room temperature and decanted to remove the excess phenyl hydrazine. The crude reaction mixture was dissolved in MeOH and 0.1 N NaOH (2:1, 0.033 M) and stirred for 3.5 hours before concentrating to dryness. Purification by column chromatography afforded the title compound 16 as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.43-6.72 (m, 1H) 7.04-7.28 (m, 1H) 7.37-7.56 (m, 4H) 7.84-8.13 (m, 2H) 8.33-8.55 (m, 1H) 11.99 (s, 1H).

Workup

  1. customdecanted
  2. customto remove the excess phenyl hydrazine
  3. customThe crude reaction mixture
  4. concentrationbefore concentrating to dryness
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-4b15992f911045ce9400a9b82eb256b9
Source dataset
uspto-grants-2015_04
Patent number
US09012470B2

Reaction notes

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