Hydrazine → HCID 178487769, compound

HRID 1818715Notes

Reaction equation

HRID 1818715 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:8]([O:20][CH3:21])=[CH:9][CH:10]=[C:11]([C:16](OC)=[O:17])[C:12]=2[C:13](=O)[CH:14]=1)=[O:4].[NH2:22][NH2:23]>CCO>[CH3:21][O:20][C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[O:17])[NH:23][N:22]=[C:13]3[CH:14]=[C:5]([C:3]([OH:2])=[O:4])[NH:6][C:7]=1[C:12]=23

Participants

4

Reactant 2

HCID 9321HydrazineHCID 58959717HCID 58959717, compound

Product 1

HCID 178487769HCID 178487769, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
68 °C

Procedure

6-Methoxy-3-oxo-2,7-dihydro-3H-pyrido[4,3,2-de]phthalazine-8-carboxylic acid hydrozide (39) To a suspension of 38 (0.45 g, 1.54 mmol) in EtOH (20 mL) was added hydrazine (1 mL) at room temperature. The reaction mixture was heated at 68° C. for 1.5 h and then cooled to room temperature. The resulting precipitate was filtered and washed with Et2O to afford a white solid (39, 0.31 g, 74%). 1H NMR (DMSO-d6, 300 MHz) δ 10.5 (br s, 1H), 9.0 (br s, 1H), 7.15-7.25 (m, 2H), 7.1 (br s, 1H), 6.8 (br s, 1H), 4.90 (br s, 2H), 4.03 (s, 3H). Mp: 305-307° C.; Anal. Calcd for C12H11N5O3.(0.75H2O): C, 50.26; H, 4.39; N, 24.42. Found: C, 50.33; H, 4.46; N, 22.04.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with Et2O
  4. customto afford a white solid (39, 0.31 g, 74%)

Sources & evidence

ORD record
ord-249602fc9d834ba785cdc7f2cf0f763c
Source dataset
uspto-grants-2009_10
Patent number
US07601719B2

Reaction notes

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