Cyanoacetamide → HCID 178426619, compound

HRID 1887998Notes

Reaction equation

HRID 1887998 reaction equation
N1CCCCC1.O[CH:8]=[C:9]([CH3:13])[C:10](=O)[CH3:11].[Na].[C:15]([CH2:17][C:18]([NH2:20])=[O:19])#[N:16]>C(O)(=O)C.O>[OH:19][C:18]1[N:20]=[C:10]([CH3:11])[C:9]([CH3:13])=[CH:8][C:17]=1[C:15]#[N:16]

Participants

7

Reactant 4

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 335011HCID 335011, compoundHCID 5360545Sodium

Product 1

HCID 178426619HCID 178426619, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Acetic acid (7.93 mL) was treated sequentially with piperidine (13.6 mL), water (208 mL), 4-hydroxy-3-methylbut-3-en-2-one, sodium salt (31.7 g, 0.257 mol) then 2-cyanoacetamide (23.8 g, 0.283 mol) then heated to reflux for 6 hours. The reaction mixture was then cooled to <20° C., treated with acetic acid (28.3 mL), stirred for 10 minutes at 0° C., then filtered and washed with water (200 mL) to yield 2-hydroxy-5,6-dimethylnicotinonitrile. To the wet solid was added 6N hydrochloric acid (200 mL) and the mixture was heated to reflux for 3 days. The cooled reaction mixture was poured into ice-water and basified with concentrated ammonium hydroxide (200 mL) and stirred for 10 minutes. The mixture was filtered, washed with water and dried under vacuum at 60° C. to yield 5,6-dimethylpyridin-2-ol (9.57 g, 22%). 400 M Hz 1H NMR (DMSO-d6) δ: 11.19 (s, 1H), 7.19 (d, 1H), 6.04 (d, 1H), 2.09 (s, 3H), 1.91 (s, 3H).

Workup

  1. temperatureto reflux for 6 hours
  2. temperatureThe reaction mixture was then cooled to <20° C.
  3. filtrationfiltered
  4. washwashed with water (200 mL)

Sources & evidence

ORD record
ord-238c163ff115402f86878826ab4d1ea0
Source dataset
uspto-grants-2013_08
Patent number
US08501770B2

Reaction notes

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