Hydrochloric Acid → HCID 14233860, compound

HRID 34656Notes

Reaction equation

HRID 34656 reaction equation
[BH4-].[Na+].[OH-:3].[Na+].[I-].[NH2:6][C:7]1[N:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH:11]3[N:17]([CH3:21])[CH:18]=[CH:19][CH:20]=[C:10]3[C:9]=2[NH+:8]=1.Cl>CO.O>[OH-:3].[NH4+:6].[CH3:21][N:17]1[CH:11]2[CH2:12][CH2:13][C:14]3[CH:15]=[N:16][C:7]([NH2:6])=[N:8][C:9]=3[C:10]2=[CH:20][CH2:19][CH2:18]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 178480186HCID 178480186, compound

Product 2

HCID 14923Ammonium HydroxideHCID 14233860HCID 14233860, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 1.78 g (47.0 mmol) of sodium borohydride in 100 ml of methanol, containing 10 ml of 6N sodium hydroxide, is added dropwise with stirring a solution of 3.20 g (9.41 mmol) of 2-amino-5,6-dihydro-7-methylpyrido[2,3-h]quinazolinium iodide, in 200 ml of a mixture of methanol and water (1:1). The solution is stirred at room temperature for 2 hours, cooled, acidified by dropwise addition of 10% hydrochloric acid and stirred at room temperature for 2 hours. The solution is concentrated, basified with concentrated ammonium hydroxide and extracted with chloroform. The chloroform extract is dried over magnesium sulfate, filtered and concentrated to a brown oil. Medium pressure chromatography (silica gel, 2% ammonium hydroxide--2% methanol--96% ethyl acetate) affords 0.45 g (22.2%) of the title compound as an orange solid; mp 204°-213° C.

Workup

  1. additionis added dropwise
  2. temperaturecooled
  3. stirringstirred at room temperature for 2 hours
  4. concentrationThe solution is concentrated
  5. extractionextracted with chloroform
  6. extractionThe chloroform extract
  7. dry with materialis dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to a brown oil

Sources & evidence

ORD record
ord-1879f44ee63a4c328031beb1a08aee1b
Source dataset
uspto-grants-1988_08
Patent number
US04762843

Reaction notes

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