Ammonium Hydroxide → HCID 16749041, compound

HRID 1911287Notes

Reaction equation

HRID 1911287 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:14])[CH3:13])[N:2]=1.[N+:15]([O-])([O-:17])=[O:16].[K+].[NH4+].[OH-]>OS(O)(=O)=O>[N+:15]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[C:3]([NH:11][C:12](=[O:14])[CH3:13])[N:2]=[CH:1]2)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 12366594N-(Isoquinolin-3-yl)acetamide

Product 1

HCID 16749041HCID 16749041, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of N-(isoquinolin-3-yl)acetamide (3.89 g, 20.9 mmol) in concentrated H2SO4 (40 mL) was cooled to 0° C. and solid potassium nitrate (2.53 g, 25.1 mmol) was added slowly in portions over 10 min. After stiffing for 1 h at 0° C., the reaction mixture was poured over ice (50 g), and neutralized with concentrated NH4OH solution. The resulting yellow solid was collected by vacuum filtration, washed with water, and dried in the vacuum oven at ambient temperature for 48 hours. This material was triturated with 1:1 CH3OH—CH2Cl2, collected by filtration, washed with CH2Cl2, and dried under vacuum. This provided 4.14 g of the title compound as a yellow solid in approximately 60% purity. MS (ESI+) m/z 232 (M+H)+.

Workup

  1. filtrationThe resulting yellow solid was collected by vacuum filtration
  2. washwashed with water
  3. customdried in the vacuum oven at ambient temperature for 48 hours
  4. customThis material was triturated with 1:1 CH3OH—CH2Cl2
  5. filtrationcollected by filtration
  6. washwashed with CH2Cl2
  7. customdried under vacuum

Sources & evidence

ORD record
ord-5047e92fa05c44beb2628e2f6cc0c392
Source dataset
uspto-grants-2013_12
Patent number
US08604053B2

Reaction notes

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