Sodium Hydroxide → 5-[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-pyridine-2-carboxylic acid amide

HRID 1784849Notes

Reaction equation

HRID 1784849 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=2)[CH:5]=[C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[CH:11][NH:12]3)[CH:7]=1.[OH-:26].[Na+]>CO.O.OO>[OH:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]([NH2:25])=[O:26])=[N:22][CH:23]=2)[CH:5]=[C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[CH:11][NH:12]3)[CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 156029935-[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-pyridine-2-carbonitrile

Product 1

HCID 156028905-[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-pyridine-2-carboxylic acid amideYield 66%

Reagents, catalysts & solvents 3

HCID 784Hydrogen PeroxideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-pyridine-2-carbonitrile (83 mg, 0.25 mmol) in MeOH (1 mL) was added 50% NaOH solution in H2O (200 μL) and 30% H2O2 (500 μL), and the mixture was stirred for 16 h at room temperature. The solution was concentrated to half the volume with a gentle stream of nitrogen, and the solution was diluted by addition of water (2 mL). The aqueous solution was extracted with ethyl acetate (2 mL, three times). The combined solution of organic layer was dried and concentrated to give 5-[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-pyridine-2-carboxylic acid amide (58 mg, 0.168 mmol, 66%) as a solid. 1H NMR (400 MHz, CD3OD) δ 8.34 (dd, J=2.4, 0.4 Hz, 1H), 7.91 (dd, J=8.8, 0.4 Hz, 1H), 7.55 (m, 1H), 7.35 (dd, J=8.0, 0.4 Hz, 1H), 7.25 (d, J=3.2 Hz, 1H), 7.14 (t, J=7.8 Hz, 1H), 7.06 (dt, J=7.2, 0.8 Hz, 1H), 6.97 (m, 1H), 6.82 (m, 1H), 6.67 (m, 1H), 6.63 (dd, J=2.4, 0.4 Hz, 1H).

Workup

  1. concentrationThe solution was concentrated to half the volume with a gentle stream of nitrogen
  2. additionthe solution was diluted by addition of water (2 mL)
  3. extractionThe aqueous solution was extracted with ethyl acetate (2 mL, three times)
  4. customThe combined solution of organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c09b2d0ce09a4446b2e1f8618d3f89ac
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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