Hydrochloric Acid → HCID 19386776, compound

HRID 2399270Notes

Reaction equation

HRID 2399270 reaction equation
[N+]([O-])([O-])=O.[Na+].[CH2:6]([O:9][C:10]1[CH:11]=[C:12]([C:16](N)=[CH:17][C:18]=1[O:19][CH2:20][CH:21]=[CH2:22])[C:13]([OH:15])=[O:14])[CH:7]=[CH2:8].Cl.C(=O)([O-])[O-].[K+].[K+].[Cu:31]Cl.[O-:33][C:34]#[N:35].[Na+]>O>[Cu:31][O:33][C:34]#[N:35].[CH2:6]([O:9][C:10]1[CH:11]=[C:12]([C:16]([C:34]#[N:35])=[CH:17][C:18]=1[O:19][CH2:20][CH:21]=[CH2:22])[C:13]([OH:15])=[O:14])[CH:7]=[CH2:8]

Participants

9

Reactant 6

HCID 313Hydrochloric Acid2×HCID 11430Potassium CarbonateHCID 24268Sodium NitrateHCID 62652Cuprous chlorideHCID 517096Sodium CyanateHCID 19386786HCID 19386786, compound

Product 2

HCID 19386776HCID 19386776, compoundHCID 178514058HCID 178514058, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
50 °C

Procedure

A solution of sodium nitrate (2.0 mmol) in water (1 ml) was slowly added to a stirred suspension of 3,4-diallyloxy-6-aminobenzoic acid (1.8 mmol) in a 2N aqueous solution of hydrochloric acid (5 ml) at 0° C. Water (10 ml) was added and the reaction mixture stirred for 30 minutes. The pH of the mixture was adjusted to pH8 by the addition of solid potassium carbonate. A solution of copper (I) cyanate was prepared by dissolving copper (I) chloride (2.25 mmol) in a solution of sodium cyanate (6.3 mmol) in water (5 ml). This was added to the rection mixture. The resulting mixture was slowly warmed to 50° C. and stirred for 20 minutes. The mixture was then heated on a steam bath for 20 minutes and acidified with a 5N aqueous solution of hydrochloric acid. This solution was extracted with ethyl acetate. The organic phase was washed with a 5N aqueous solution of hydrochloric acid and a saturated aqueous solution of sodium chloride. The organic phase was then extracted with a saturated aqueous solution of sodium hydrogen carbonate. The aqueous phase was acidified and extracted with ethyl acetate. This organic phase was washed with a saturated aqueous solution of sodium chloride and dried (MgSO4). The solvent was evaporated to give 3,4-diallyloxy-6-cyanobenzoic acid as a light orange solid. NMR (DMSO-d6): 4.73(m,4H); 5.35(m,4H); 6.04(m,2H); 7.48(s,1H); 7.57(s,1H): M/S CI (M+H)+= 260.

Workup

  1. additionThis was added to the rection mixture
  2. stirringstirred for 20 minutes
  3. temperatureThe mixture was then heated on a steam bath for 20 minutes
  4. extractionThis solution was extracted with ethyl acetate
  5. washThe organic phase was washed with a 5N aqueous solution of hydrochloric acid
  6. extractionThe organic phase was then extracted with a saturated aqueous solution of sodium hydrogen carbonate
  7. extractionextracted with ethyl acetate
  8. washThis organic phase was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried (MgSO4)
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-43521e9c7bf24af49725e06605be541d
Source dataset
uspto-grants-1995_09
Patent number
US05447925

Reaction notes

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