4-Aminophenol → HCID 135964711, compound

HRID 1951296Notes

Reaction equation

HRID 1951296 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)=[N:12][N:11]=1.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>CC(O)CC.C(Cl)Cl>[CH3:26][N:23]1[CH2:22][CH2:21][N:20]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=3)=[N:11][N:12]=2)[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 4034-AminophenolHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 11184602HCID 11184602, compound

Product 1

HCID 135964711HCID 135964711, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6568(+-)-2-ButanolSolvent

Procedure

A mixture of 4-aminophenol (42 mg, 0.38 mmol), 1-chloro-4-(4-methylpiperazin-1-yl)phthalazine (100 mg, 0.381 mmol), and TFA (29 μl, 0.38 mmol) was heated in 2-butanol (3 mL) in a sealed tube at 90° C. overnight. Next day LC/MS shows completion of reaction. The reaction was cooled and diluted with DCM. Aqueous sodium bicarbonate was added and the organic layer was collected. The aqueous layer was neutralized with 1N HCl and the product was extracted with DCM. The organic layers were combined, dried over sodium sulfate, and concentrated to afford 4-(4-(4-methylpiperazin-1-yl)phthalazin-1-ylamino)phenol as solid brown material. MS: Found M+H+=336.2. Calc'd for C19H21N5O: 335.4.

Workup

  1. customcompletion of reaction
  2. temperatureThe reaction was cooled
  3. customthe organic layer was collected
  4. extractionthe product was extracted with DCM
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-40b91a155ffa4a4185f89c1e5a50cf13
Source dataset
uspto-grants-2013_03
Patent number
US08404694B2

Reaction notes

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