Water → HCID 178439203, compound

HRID 1783679Notes

Reaction equation

HRID 1783679 reaction equation
Cl.[CH:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH2:12])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[C:13]1(=O)[O:18][C:16](=[O:17])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.O.C([O-])(O)=O.[Na+]>CC(O)=O>[OH:18][C:13]1[C:14]2[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16](=[O:17])[N:11]([C:8]2[CH:9]=[CH:10][C:5]([CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=2)[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 516892Sodium BicarbonateHCID 2733248[4-(Propan-2-yl)phenyl]hydrazine hydrochloride

Product 1

HCID 178439203HCID 178439203, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

4-Isopropyl phenyl hydrazine hydrochloride (2.77 g, 14.6 mmol) was added in one portion to a stirred mixture of phthalic anhydride (2.0 g, 13 mmol) in HOAc (25 ml) at RT. The reaction mixture was heated to 125° C. for 2 hours, and then allowed to cool to RT. The resultant suspension was poured into H2O (100 ml), NaHCO3 solution (1M) was added and the resulting solid was removed by filtration. The mother liquor was acidified with conc. HCl. The resulting solid was collected by filtration and dried in vacuum to give the title compound (1.62 g, 45% yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO) 11.80 (1H, s), 8.30 (1H, d), 7.92-8.01 (3H, m), 7.92 (2H, d), 7.35 (2H, d), 2.96 (1H, m), 1.25 (6H, d); MS (ESI+)=345.12 (M+H)+.

Workup

  1. temperatureto cool to RT
  2. additionwas added
  3. customthe resulting solid was removed by filtration
  4. filtrationThe resulting solid was collected by filtration
  5. customdried in vacuum

Sources & evidence

ORD record
ord-e033c88dbfea4a5d8f728e30e14989a2
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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