Ammonium Hydroxide → HCID 20570350, compound

HRID 1577934Notes

Reaction equation

HRID 1577934 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:16][CH2:17][CH:18]([OH:21])[CH2:19][Cl:20])=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH2:11][CH2:10]2)[C:2]#[CH:3].[OH-].[NH4+:23]>CO>[ClH:20].[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:16][CH2:17][CH:18]([OH:21])[CH2:19][NH2:23])=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH2:11][CH2:10]2)[C:2]#[CH:3]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 20570384HCID 20570384, compound

Product 1

HCID 20570350HCID 20570350, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

1.0 g of 8-(2-propynyloxy)-5-(3-chloro-2-hydroxypropoxy)-3,4-dihydrocarbostyril was dissolved in 30 ml of methanol, and 4.5 ml of 28% ammonium hydroxide was added to the solution followed by heating at 70° C. for 10 hours. The methanol and the ammonium hydroxide were evaporated under reduced pressure, and the residue was made acidic with hydrochloric acid and washed with ethyl acetate. The aqueous layer was separated, made alkaline with sodium hydroxide, extracted with chloroform, washed with water and then dried over anhydrous sodium sulfate. The chloroform was evaporated under reduced pressure, and the residue was purified by silica gel chromatography, and the product was converted to the hydrochloride thereof by adding methanol-hydrochloric acid. Recrystallization from methanol-diethyl ether afforded 0.5 g of 8-(2-propynyloxy)-5-(3-amino-2-hydroxypropoxy)-3,4-dihydrocarbostyril hydrochloride having a melting point of 196.5°-198° C.

Workup

  1. customThe methanol and the ammonium hydroxide were evaporated under reduced pressure
  2. washwashed with ethyl acetate
  3. customThe aqueous layer was separated
  4. extractionextracted with chloroform
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe chloroform was evaporated under reduced pressure
  8. customthe residue was purified by silica gel chromatography
  9. additionby adding methanol-hydrochloric acid
  10. customRecrystallization from methanol-diethyl ether

Sources & evidence

ORD record
ord-12c0376a35594edd889e3467821520d1
Source dataset
uspto-grants-1981_09
Patent number
US04289883

Reaction notes

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