Acetic Acid → HCID 178516244, compound

HRID 1013655Notes

Reaction equation

HRID 1013655 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:12][N:11]=2)=[CH:5][CH:4]=1.Br.C(O)(=O)C.[OH-].[Na+]>>[C:20]1([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[N:8][CH:7]=3)=[N:11][N:12]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 67318044HCID 67318044, compound

Product 1

HCID 178516244HCID 178516244, compound

Conditions

Temperature
130 °C

Procedure

In a 25 RBF was added N-(6-methoxypyridin-3-yl)-4-phenylphthalazin-1-amine (290 mg, 0.88 mmol), hydrobromic acid (2.4 mL, 44.2 mmol) and acetic acid (2.5 mL, 43.3 mmol), and a reflux condenser open to air was fitted and the RBF was heated to 130° C., while stirring, for 2 h. The reaction was cooled to RT, the mixture neutralized with 6N NaOH, upon which a yellow solid crashed out. The yellow solid was filtered, washed with water, placed in vacuum oven at 30° C. to dry, to afford 5-(4-phenylphthalazin-1-ylamino)pyridin-2-ol, as light yellow solid. MS [M+H]=315.2. Calc'd for C19H14N4O: 314.3.

Workup

  1. customwas fitted
  2. temperatureThe reaction was cooled to RT
  3. filtrationThe yellow solid was filtered
  4. washwashed with water
  5. customplaced in vacuum oven at 30° C.
  6. customto dry

Sources & evidence

ORD record
ord-249f35467ae14d0db937f116bc2d5bc5
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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