Hydrochloric Acid → HCID 10925187, compound

HRID 1743355Notes

Reaction equation

HRID 1743355 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]([O:24]C)=[O:23])=[CH:20][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].CO.Cl>O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]([OH:24])=[O:23])=[CH:20][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 9967388HCID 9967388, compound

Product 1

HCID 10925187HCID 10925187, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-benzyl-3-(5-methoxycarbonyl-2-furyl)-1H-indazole (1.46 g, 4.39 mmol), 15% aqueous KOH solution (100 mL) and methanol (100 mL) was heated to reflux for 4 h. The resultant solution was allowed to cool and then diluted with H2O (300 mL). The solution was acidified to pH 2 by the addition of conc. HCl and the precipitate collected by vacuum filtration. The off-white solid was washed with H2O and air dried. Recrystallisation of the crude solid (EtOH) gave the product as fine off-white needles (1.16 g, 83%): mp 205–206.5° C. (lit mp 200–202° C.); 1H-NMR (DMSO) 5.34 (s, 2H), 6.67 (d, 1H, J=3.6 Hz), 6.89–7.00 (m, 7H), 7.08 (m, 2H), 7.89 (d, 1H, J=8.0 Hz); 13C-NMR (CDCl3) 52.55, 109.06, 110.91, 119.84, 120.91, 121.22, 122.57, 127.49, 127.69(2C), 128.02, 128.99(2C), 134.69, 137.40, 140.72, 144.41, 151.75, 159.67; MS (EI) M+; Anal. (C19H14N2O3) C, calcd 73.19; found 73.18, H, calcd 7.17; found 7.16, N, calcd 14.23; found 14.13.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. temperatureto cool
  4. filtrationthe precipitate collected by vacuum filtration
  5. washThe off-white solid was washed with H2O and air
  6. customdried
  7. customRecrystallisation of the crude solid (EtOH)

Sources & evidence

ORD record
ord-6d64769bb2244c218e9ba314df061fb1
Source dataset
uspto-grants-2006_03
Patent number
US07009056B2

Reaction notes

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