Sodium Hydroxide → HCID 178470073, compound

HRID 64201Notes

Reaction equation

HRID 64201 reaction equation
N[C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.N([O-])=[O:18].[Na+].[OH-].[Na+]>OS(O)(=O)=O>[OH:18][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14942910HCID 14942910, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178470073HCID 178470073, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of ethyl 3-aminoisoquinoline-4-carboxylate (583 mg, 2.70 mmol) in 6.8 mL of H2SO4 5 N cooled to 0° C. was added sodium nitrite (223 mg, 3.24 mmol, dissolved in 1 mL of water). The reaction mixture was stirred at 0° C. for 2.5 h and then NaOH(aq) 1N was added until pH=7. The aqueous phase was extracted twice with DCM and the combined organic phases were dried over MgSO4, filtered and evaporated to give the title compound of Step A which was used without further purification in the next step (583 mg, 99%). MS (ESI) mass calcd. for C12H11NO3, 217.1. m/z found 218.1 [M+H]+.

Workup

  1. extractionThe aqueous phase was extracted twice with DCM
  2. dry with materialthe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-b08f3ab82905449081a7c3f314d9d1ff
Source dataset
uspto-grants-2016_09
Patent number
US09447117B2

Reaction notes

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