Hydrochloric Acid → 1-Hydroxyethyl radical

HRID 1585656Notes

Reaction equation

HRID 1585656 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Cl.[CH3:20][OH:21]>[Pd]>[NH2:1][C:2]1[N:3]=[C:4]([C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:5]=[C:6]2[C:11]=1[NH:10][CH2:9][CH2:8][CH2:7]2.[CH2:20]([O-:21])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 11118031HCID 11118031, compound

Product 2

HCID 1194401-Hydroxyethyl radicalHCID 21219098HCID 21219098, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Hydrogenate a mixture of 8-amino-6-(3-methyl-2-pyridinyl)-1,7-naphthyridine (10.0 g, 0.0425 mol) and 5% palladium-on-carbon (0.52 g) in methanol (150 mL) at 50 psi for 18 hours. Acidify with 3.4 M ethereal hydrochloric acid (12.5 mL, 0.0425 mol), dilute with methanol (200 mL) and continue hydrogenation for another 24 hours. Filter the reaction mixture through Celite, evaporate the filtrate under reduced pressure and triturate the residue in diethyl ether (450 mL). Filter and crystallize the isolated solids to obtain the hydrochloride salt of 8-amino-1,2,3,4-tetrahydro-6-(3-methyl-2-pyridinyl)-1,7-naphthyridine as a 0.1 ethanolate, C14H16N4, mp 255-257° C. (dec). CIMS: MH+ 241 (100%).

Workup

  1. customfor another 24 hours
  2. filtrationFilter the reaction mixture through Celite
  3. customevaporate the filtrate under reduced pressure
  4. customtriturate the residue in diethyl ether (450 mL)
  5. filtrationFilter
  6. customcrystallize the isolated solids

Sources & evidence

ORD record
ord-227c0fd00ae44786a0a03ae6af198e4a
Source dataset
uspto-grants-1999_08
Patent number
US05939431

Reaction notes

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