Acetic Acid → 4-((4-Phenylphthalazin-1-yl)methyl)phenol

HRID 2361028Notes

Reaction equation

HRID 2361028 reaction equation
C[O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:10][N:9]=2)=[CH:5][CH:4]=1.C(O)(=O)C.Br>O.[OH-].[Na+]>[C:18]1([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:25][CH:24]=3)=[N:9][N:10]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 667316721-(4-Methoxybenzyl)-4-phenylphthalazine

Product 1

HCID 577562584-((4-Phenylphthalazin-1-yl)methyl)phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To 1-(4-methoxybenzyl)-4-phenylphthalazine (0.240 g, 0.735 mmol) was added acetic acid (1.5 mL) followed by hydrobromic acid 48% (1.50 ml, 27.6 mmol). A water condenser was attached and the mixture was heated to reflux for 3 hours. The reaction was diluted with water and neutralized with 6 N NaOH until pH˜6. Filtered the resulting solid, washed with water and dried to yield 4-((4-phenylphthalazin-1-yl)methyl)phenol as an off-white solid. MS m/z=313 [M+1]+. Calc'd for C21H16N2O: 312.37.

Workup

  1. customA water condenser was attached
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 3 hours
  4. filtrationFiltered the resulting solid
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-16b2f2e734af4a829195fac933f6346f
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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