Hydrazine → HCID 178424144, compound

HRID 2357556Notes

Reaction equation

HRID 2357556 reaction equation
C([N:4](C(C)C)[C:5](=[O:21])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:8][C:7]=1[CH:19]=O)(C)C.[NH2:25]N>C(O)(=O)C>[C:13]1([CH3:18])[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:9]1[CH:8]=[C:7]2[C:6](=[CH:11][CH:10]=1)[C:5]([OH:21])=[N:4][N:25]=[CH:19]2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86607610HCID 86607610, compound

Product 1

HCID 178424144HCID 178424144, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of N,N-diisopropyl 2-formyl-4-(2-methylphenyl)benzamide (5.45 g, 12 mmol) in acetic acid (15 mL) was added anhydrous hydrazine (0.56 mL, 18 mmol). The resulting solution was then heated at 110° C. for 16 h. The reaction mixture was cooled to RT, and the volatiles removed in vacuo. The residue was diluted with ethyl acetate (150 mL) and washed with saturated aqueous solution of sodium bicarbonate, and brine. The resulting organic solution was then dried over magnesium sulfate and concentrated under reduced pressure to give 6-o-tolylphthalazin-1-ol as a yellow solid. MS (ESI, pos.ion) m/z: 237.2 (M+1)

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customthe volatiles removed in vacuo
  3. additionThe residue was diluted with ethyl acetate (150 mL)
  4. washwashed with saturated aqueous solution of sodium bicarbonate, and brine
  5. dry with materialThe resulting organic solution was then dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3d32dd02a2454bf5b3301b7edc0fc63b
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

Loading…