Sodium Hydroxide → HCID 16124640, compound

HRID 1882198Notes

Reaction equation

HRID 1882198 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3N=N2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>P(=O)(O)(O)O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][C:12]=1[NH:8]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58880038HCID 58880038, compound

Product 1

HCID 16124640HCID 16124640, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
150 °C

Procedure

Compound 3 (2.8 g, 10.2 mmol) was dissolved in ortho-phosphoric acid (40 ml). The mixture was heated to 150° C. for 18 hours, and the intended product confirmed by LC-MS. The mixture was cooled to 0° C. and the acid neutralized with concentrated NaOH. Extraction with methylene chloride afforded a mixture of Compounds 4 and 4′, which was then purified by HPLC to provide Compound 4 (180 mg, 9%). 1H NMR (400 MHz, CD3OD) δ 9.16 (d, J=7.8 Hz 1H) 8.48 (s, 1H) 7.62 (d, J=7.8 Hz 1H) 7.52 (d, J=6.8 Hz 1H) 7.44 (m, 2H). [M+H] calc'd for C17H12N2, 245; found 245.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionExtraction with methylene chloride
  3. customafforded
  4. customwas then purified by HPLC

Sources & evidence

ORD record
ord-9acff117f21941fba75577eff7f280b9
Source dataset
uspto-grants-2012_11
Patent number
US08318939B2

Reaction notes

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