Methanol → HCID 57545983, compound

HRID 913882Notes

Reaction equation

HRID 913882 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#N)[C:8]2[C:4](=[CH:5][N:6]([CH:13]3[CH2:15][CH2:14]3)[N:7]=2)[CH:3]=1.[OH-:16].[Na+].C[OH:19]>>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]([OH:19])=[O:16])[C:8]2[C:4](=[CH:5][N:6]([CH:13]3[CH2:15][CH2:14]3)[N:7]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57545942HCID 57545942, compound

Product 1

HCID 57545983HCID 57545983, compound

Conditions

Temperature
110 °C

Procedure

A microwave tube was charged 5-chloro-2-cyclopropyl-2H-indazole-7-carbonitrile (0.54 g, 2.5 mmol), methanol (8.0 mL) and a 4 N sodium hydroxide solution (5 mL, 20 mmol). The tube was sealed and heated at 110° C. for 3 h via microwave. After cooling to room temperature, the mixture was concentrated in vacuo to remove most of the methanol. The residue was poured into water/ethyl acetate. The product was extracted with water (2×) and the organics discarded. The aqueous layers were pooled together and acidified to pH 2.0 with 1 N hydrochloric acid. The resulting precipitate was filtered and dried in vacuo for several hours to afford 0.47 g (80%) as a white powder. 1H-NMR (CD3OD, 300 MHz) δ 8.40 (s, 1H), 7.94-7.95 (m, 2H), 4.08-4.14 (m, 1H), 1.37-1.42 (m, 2H), 1.21-1.23 (m, 2H). Mass spec.: 237.16 (MH)+.

Workup

  1. customThe tube was sealed
  2. temperatureAfter cooling to room temperature
  3. concentrationthe mixture was concentrated in vacuo
  4. customto remove most of the methanol
  5. additionThe residue was poured into water/ethyl acetate
  6. extractionThe product was extracted with water (2×)
  7. filtrationThe resulting precipitate was filtered
  8. customdried in vacuo for several hours
  9. customto afford 0.47 g (80%) as a white powder

Sources & evidence

ORD record
ord-a76a131b69c844a98ad997d14bbb45b1
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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