Acetone Cyanohydrin → HCID 68185069, compound

HRID 883662Notes

Reaction equation

HRID 883662 reaction equation
C(=O)([O-])[O-].[K+].[K+].CC(C)(O)[C:9]#[N:10].[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:18](=[O:28])/[C:17]/2=[C:29](/[C:34]#[N:35])\[C:30]([O:32][CH3:33])=[O:31]>O.O1CCCC1>[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:18](=[O:28])[C:17]2([CH:29]([C:34]#[N:35])[C:30]([O:32][CH3:33])=[O:31])[C:9]#[N:10]

Participants

6

Reactant 3

HCID 6406Acetone CyanohydrinHCID 11430Potassium CarbonateHCID 67424029HCID 67424029, compound

Product 1

HCID 68185069HCID 68185069, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of potassium carbonate (1.39 g, 10.03 mmol) in water (8.2 ml) was treated with acetone cyanohydrine (4.0 ml, 43.5 mmol) at ambient temperature and continuously stirred for 15 min. A fine suspension of methyl (2Z)-[5-chloro-1-(2-methoxy-2-oxoethyl)-2-oxo-1,2-dihydro-3H-indol-3-ylidene](cyano)acetate, intermediate 45, (11.19 g, 33.43 mmol) in tetrahydrofuran (500 ml) was added dropwise and the resulting suspension was heated to reflux for 3 hours. The solid was filtered off, the residue was washed with tetrahydrofuran (3×40 ml) and the collected filtrates were evaporated to dryness. The solid was dissolved in dichloromethane (250 ml), washed with saturated NaHCO3 (2×100 ml), water (100 ml) and dried (MgSO4) to obtain the title compound (10.82 g, 89%) as red-brown solid (HPLC purity: 91%). MS (ESI+): 362.2; MS (ESI−): 360.2

Workup

  1. additionwas added dropwise
  2. temperaturethe resulting suspension was heated
  3. temperatureto reflux for 3 hours
  4. filtrationThe solid was filtered off
  5. washthe residue was washed with tetrahydrofuran (3×40 ml)
  6. customthe collected filtrates were evaporated to dryness
  7. dissolutionThe solid was dissolved in dichloromethane (250 ml)
  8. washwashed with saturated NaHCO3 (2×100 ml), water (100 ml)
  9. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-e77181c8375346db8e6854edaa48f905
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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