Sodium Hydroxide → HCID 67481594, compound

HRID 509528Notes

Reaction equation

HRID 509528 reaction equation
[NH2:1][C:2]1[N:19]=[CH:18][C:17]([Br:20])=[CH:16][C:3]=1[C:4]([NH:6][NH:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[OH-].[Na+]>O>[Br:20][C:17]1[CH:16]=[C:3]([C:4]2[O:15][C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:7][N:6]=2)[C:2]([NH2:1])=[N:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67479813HCID 67479813, compound

Product 1

HCID 67481594HCID 67481594, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Polyphosphonic acid (4.006 mL of 84% w/v, 41.04 mmol) was heated to 100° C. and treated with 2-amino-N′-benzoyl-5-bromonicotinohydrazide (673 mg, 1.626 mmol) in portions over a period of 25 minutes. The reaction mixture was allowed to stir for 2 hours at 110° C. and then allowed to cool to ambient temperature. Water was added and the mixture basified (using 1M NaOH) and extracted with DCM (×3). The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give the product as a white solid (372 mg, 72% Yield). 1H NMR (400.0 MHz, DMSO) δ 7.54 (s, 2H), 7.62-7.68 (m, 3H), 8.22-8.25 (m, 2H), 8.32 (d, J=2.5 Hz, 1H) and 8.50 (d, J=2.5 Hz, 1H) ppm; MS (ES+) 318.86.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with DCM (×3)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-930a9730905e4de18d7f1213bf7c3a48
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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