Sodium Hydroxide → HCID 22480095, compound

HRID 1353719Notes

Reaction equation

HRID 1353719 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[N:19])[CH:16]=3)[NH:11][N:10]=2)=[CH:5][CH:4]=1.[OH-:21].[Na+]>Cl>[CH3:1][N:2]([CH3:20])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([NH2:19])=[O:21])[CH:16]=3)[NH:11][N:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22479912HCID 22479912, compound

Product 1

HCID 22480095HCID 22480095, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-[4-(dimethylamino)phenyl]-1H-indazole-5-carbonitrile (125 mg, 0.476 mmol) in 5.00 mL of concentrated aq. HCl was heated at 47° C. for 1 h, and then added dropwise with stirring to 20 mL of 6.0 N aq. NaOH that was cooled in a water bath. The mixture was extracted with 2×EtOAc, and the combined organics were dried (Na2SO4). Purification by silica gel chromatography using EtOAc as eluent afforded the title compound (69.3 mg, 52.1% yield): 1H NMR (DMSO-d6) δ 13.19 (s, 1H), 8.58 (s, 1H), 8.10 (br s, 1H), 7.9S–7.82 (m, 3H), 7.56 (d, 1H), 7.30 (br s, 1H), 6.84 (d, 2H), 2.98 (s, 6H); ES-MS (m/z) 281 [M+1]+.

Workup

  1. additionadded dropwise
  2. temperaturewas cooled in a water bath
  3. extractionThe mixture was extracted with 2×EtOAc
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-e12adfde4297406d8f7aec08ef2e3571
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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