Sodium Hydroxide → thieno[2,3-c]pyridine-5-carboxylic acid(WXC09021)

HRID 971901Notes

Reaction equation

HRID 971901 reaction equation
[C:1]([CH:4]1[N:9](N=O)[CH2:8][C:7]2[S:12][CH:13]=[CH:14][C:6]=2[CH:5]1O)([OH:3])=[O:2].[OH-].[Na+]>C(O)C>[C:1]([C:4]1[CH:5]=[C:6]2[CH:14]=[CH:13][S:12][C:7]2=[CH:8][N:9]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21312553HCID 21312553, compound

Product 1

HCID 12277675thieno[2,3-c]pyridine-5-carboxylic acid(WXC09021)Yield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

An initially homogeneous solution of 10 g (0.044 mole) of the nitroso derivative obtained in Example 1, 20 cc ethanol and 60 cc aqueous 20% sodium hydroxide is refluxed for 2 hours. After cooling and addition of ethanol, the resulting precipitate is filtered off, washed with ethanol and then with ether, after which it is dried. The resulting sodium salt (M.p.=260° C.; 4.7 g; 60%) is treated with 23 cc (1 equivalent) N hydrochloric acid. The material is found to dissolve at first and then to reprecipitate. It is directly recrystallized after addition of 27 cc water, to give 2.5 g (32%) pink crystals, M.p.=246° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate is filtered off
  3. washwashed with ethanol
  4. dry with materialwith ether, after which it is dried
  5. additionThe resulting sodium salt (M.p.=260° C.; 4.7 g; 60%) is treated with 23 cc (1 equivalent) N hydrochloric acid
  6. dissolutionto dissolve at first and then
  7. customIt is directly recrystallized
  8. additionafter addition of 27 cc water

Sources & evidence

ORD record
ord-90353734c9a5457b8426937635a2ea2c
Source dataset
uspto-grants-1979_07
Patent number
US04161599

Reaction notes

Loading…