Hydrazine hydrate (1:1) → 1-Oxo-4-[(pyridin-4-yl)-methyl]-6-bromo-1,2-dihydrophthalazine

HRID 49879Notes

Reaction equation

HRID 49879 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6](=[C:12]1[CH:17]=[CH:16][NH:15][CH:14]=[CH:13]1)[C:5]2=O.O.[NH2:20][NH2:21]>>[O:11]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[C:5]([CH2:6][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:21][NH:20]1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178515373HCID 178515373, compound

Product 1

HCID 227420241-Oxo-4-[(pyridin-4-yl)-methyl]-6-bromo-1,2-dihydrophthalazine

Procedure

Under exclusion of air, 4.75 g (15.7 mmol) 5-bromo-2-(1H-pyridin-4-ylidene)indan-1,3-dione and 14 ml hydrazine hydrate are heated for 4 h to 130° C. Cooling, filtering, and washing with ethanol yields title compound A in the mixture with a little 1-oxo-4-[(pyridin-4-yl)-methyl]-6-bromo-1,2-dihydrophthalazine (B). A: HPLC: tRet(Grad5-40)=11.5; 1H-NMR (DMSO-d6) 12.76 (HN), 8.46 (d, J=6, 2H), 8.34 (d, J=2, 1H), 8.07 (dd, J=8, 2, 1H), 7.85 (d, J=8, 1H), 7.30 (d, J=6, 2H), 4.33 (s, 2H); B: HPLC: tRet(Grad5-40)=11.3; 1H-NMR (DMSO-d6) 12.76 (HN), 8.46 (d, J=6, 2H), 8.16 (d, J=8, 1H), 8.14 (d, J=2, 1H), 8.00 (dd, J=8, 2, 1H), 7.3 (d, J=6, 2H), 4.35 (s, 2H).

Workup

  1. temperatureCooling
  2. filtrationfiltering
  3. washwashing with ethanol

Sources & evidence

ORD record
ord-db146f4167ec4477a1664912a12a85d3
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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