Hydrochloric Acid → 4-[3-(Hydroxymethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzaldehyde

HRID 1678778Notes

Reaction equation

HRID 1678778 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:18]4=[N:28][N:29]=[C:30]([CH2:31][OH:32])[N:17]4[CH:16]=[CH:15][C:14]=3[N:13]=2)=[CH:8][CH:7]=1.Cl>C1COCC1.C(OCC)(=O)C>[OH:32][CH2:31][C:30]1[N:17]2[C:18]([C:19]3[CH:20]=[C:21]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:12]([C:9]4[CH:10]=[CH:11][C:6]([CH:2]=[O:1])=[CH:7][CH:8]=4)=[N:13][C:14]=3[CH:15]=[CH:16]2)=[N:28][N:29]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59472958{8-[4-(1,3-Dioxolan-2-yl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}methanol

Product 1

HCID 594728804-[3-(Hydroxymethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 14-1 (2.1 g, 4.9 mMol) in THF (50 mL) was added 1N HCl (50 mL). After stirring at room temperature for 30 minutes, the reaction was diluted with ethyl acetate and washed twice with water, followed by brine. The organic layer was dried with MgSO4 and Na2SO4, filtered and concentrated in vacuo to yield 14-2 as a red solid. Mass (M+1) calculated: 381.1346 observed: 381.1346.

Workup

  1. washwashed twice with water
  2. dry with materialThe organic layer was dried with MgSO4 and Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1264493ef6fb4777b70ebaa459783547
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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