Potassium Hydroxide → HCID 20147168, compound

HRID 569479Notes

Reaction equation

HRID 569479 reaction equation
[C:1]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH:20]=[C:21]([C:27]([O:29]CC)=[O:28])[C:22]([O:24]CC)=[O:23])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[OH-].[K+]>O>[C:1]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH:20]=[C:21]([C:27]([OH:29])=[O:28])[C:22]([OH:24])=[O:23])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20147155HCID 20147155, compound

Product 1

HCID 20147168HCID 20147168, compoundYield 335.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethyl 2-[3-(1-tridecynyl)-4-pyridyl]methylenepropane-1,3-dioate (0.47 g, 1.1 mmole, from Example 3) was added to a solution of potassium hydroxide (0.66 g) in water (7.5 ml) and the mixture was heated to reflux for 24 hours. The resulting clear solution was then acidified at 0° C. and the precipitated product was filtered off and washed with water. Recrystallisation of the dried material from ethyl acetate gave 1.37 g (34%) of the title compound, mp 175°-177° C., νmax (mull) 2500 (broad), 1740 cm-1 ; δ(DMSO) 0.84 (3H, distorted t, terminal CH3), 1.20 (14H, m, alkylene chain), 1.42 (2H, m, CH2 (CH2)2C≡C), 1.57 (2H, m, CH2CH2C≡C), 2.50 (2H, t, CH2C≡C), 7.41 (2H, d, J 5.1 Hz, C-5H), 7.74 (1H, s, Ar CH=C), 8.56 (1H, d, J 5.1 Hz, C-6H), 8.67 (1H, d, J 0.5 Hz, C-2H), 13.73 (2H, broad exchangeable, CO2H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 24 hours
  3. customwas then acidified at 0° C.
  4. filtrationthe precipitated product was filtered off
  5. washwashed with water
  6. customRecrystallisation of the dried material from ethyl acetate

Sources & evidence

ORD record
ord-fa019fd9fa144de6b626fe8af7bb286b
Source dataset
uspto-grants-1988_03
Patent number
US04732901

Reaction notes

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