Hydrochloric Acid → HCID 13136928, compound

HRID 851200Notes

Reaction equation

HRID 851200 reaction equation
N[C:2]1[C:3]([CH3:17])=[CH:4][C:5]2[O:15][C:14](=[O:16])[C:9]3[CH2:10][NH:11][CH2:12][CH2:13][C:8]=3[C:6]=2[CH:7]=1.N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].[ClH:28]>O>[Cl:28][C:2]1[C:3]([CH3:17])=[CH:4][C:5]2[O:15][C:14](=[O:16])[C:9]3[CH2:10][NH:11][CH2:12][CH2:13][C:8]=3[C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 11430Potassium CarbonateHCID 13136926HCID 13136926, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13136928HCID 13136928, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-5 °C

Procedure

Concentrated hydrochloric acid (8 ml) is added to a stirred suspension of 9-amino-1,2,3,4-tetrahydro-8-methyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one (1.5 g, 0.0065 moles) in water (5 ml). The solution is cooled to -5° C. and a solution of sodium nitrite (0.45 g, 0.0065 moles) in water (4 ml) is added dropwise. After 15 minutes the mixture is added to a solution of freshly prepared cuprous chloride (0.8 g, 0.008 moles) in 20% HCl (8 ml) and stirred for 15 minutes. The suspension is warmed on the steam bath for one hour, allowed to cool, and 10% aqueous potassium carbonate is added until the mixture is basic. The precipitate is filtered off, rinsed with water, dissolved in warm dilute hydrochloric acid, filtered, and reprecipitated by the addition of concentrated ammonium hydroxide. The precipiate is filtered off, rinsed with water, and dried. Recrystallization from ethyl acetate gave the product (0.8 g), mp 184°- 185° C.

Workup

  1. temperatureThe suspension is warmed on the steam bath for one hour
  2. temperatureto cool
  3. filtrationThe precipitate is filtered off
  4. washrinsed with water
  5. dissolutiondissolved
  6. temperaturein warm dilute hydrochloric acid
  7. filtrationfiltered
  8. customreprecipitated by the addition of concentrated ammonium hydroxide
  9. filtrationThe precipiate is filtered off
  10. washrinsed with water
  11. customdried
  12. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-80bf8df6347c4f9695dfa6d2923cdb4f
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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