Ethanol → HCID 59490381, compound

HRID 2383413Notes

Reaction equation

HRID 2383413 reaction equation
[Na].[C:2]1([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][C:12](=[O:17])[C:11]=3[CH:10]=[N:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18](OCC)=[O:19].C(O)C>C1(C)C=CC=CC=1.O>[O:17]=[C:12]1[CH:13]([CH:18]=[O:19])[CH2:14][CH2:15][C:16]2[N:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:9]=[CH:10][C:11]1=2

Participants

7

Reactant 4

HCID 702EthanolHCID 8025Ethyl formateHCID 47385571-phenyl-6,7-dihydro-1H-indazol-4(5H)-oneHCID 5360545Sodium

Product 1

HCID 59490381HCID 59490381, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a stirred suspension of sodium (0.75 g, 33 mmol) in toluene (200 mL) was added 1-phenyl-6,7-dihydro-1H-indazol-4(5H)-one (2.6 g, 123 mmol). The reaction mixture was stirred for 30 minutes and a solution of ethyl formate (2.22 mL, 276 mmol) in toluene (10 mL) was added over 10 minutes followed by absolute ethanol (1 mL). The reaction was stirred at room temperature for 40 hours. The reaction mixture was cautiously poured into ice-cooled water (100 mL). The organic layer was separated. The aqueous layer was extracted with diethylether (100 mL) and acidified with 6N HCl to a pH between 5 and 6. The aqueous layer was then extracted with dichloromethane (3×75 mL). The combined organic layer was dried using sodium sulfate and concentrated under reduced pressure to give a residue which on trituration with hexane gave the desired product (1.1 g, 32%) as a solid. 1H NMR (CDCl3, 400 MHz): δ 10.75 (s, 1H), 8.00 (s, 1H), 7.61-7.54 (m, 5H), 7.48-7.45 (m, 1H), 3.00-2.96 (m, 2H), 2.76-2.70 (m, 2H); LCMS [M+H]: 241.

Workup

  1. stirringThe reaction was stirred at room temperature for 40 hours
  2. additionThe reaction mixture was cautiously poured into ice-
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted with diethylether (100 mL)
  5. extractionThe aqueous layer was then extracted with dichloromethane (3×75 mL)
  6. customThe combined organic layer was dried
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue which on trituration with hexane

Sources & evidence

ORD record
ord-5440c244aeca43cd99499124fa7b3d65
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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