HCID 86666548, compound → HCID 67953939, compound

HRID 1916852Notes

Reaction equation

HRID 1916852 reaction equation
[Br-].[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][N+:4]=1[CH:10]([C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:11]>CO>[F:9][C:6]1[CH:7]=[CH:8][C:3]2[N:4]([C:10]([CH3:11])=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:2]=2)[CH:5]=1

Participants

3

Reactant 1

HCID 86666548HCID 86666548, compound

Product 1

HCID 67953939HCID 67953939, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 5-C (5.35 g, 16.7 mmol) in MeOH (75 mL), was heated at reflux for 6 hours. The solution was cooled to rt, and the solvent was evaporated in vacuo. The residue was dissolved in water and made basic with aqueous NaHCO3, to give a solid precipitate. The solid was collected by filtration, dissolved into EtOAc, and dried over sodium sulfate. The solvent was evaporated in vacuo to give compound 5-D as a pale pink solid (3.4 g, 92%). 1H-NMR (CDCl3): δ 7.82-7.86 (m, 1H), 7.64-7.68 (m, 1H), 7.15-719 (m, 1H), 4.47 (q, J=7.1 Hz, 2H), 2.78 (s, 3H), 1.46 (t, J=7.1 Hz, 3H); MS: m/z 223.0 (MH+)

Workup

  1. temperatureat reflux for 6 hours
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. customto give a solid precipitate
  5. filtrationThe solid was collected by filtration
  6. dissolutiondissolved into EtOAc
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated in vacuo
  9. customto give compound 5-D as a pale pink solid (3.4 g, 92%)

Sources & evidence

ORD record
ord-d90e66f233514d74a714d137c833b30f
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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