HCID 612783, compound → HCID 86686660, compound

HRID 2404236Notes

Reaction equation

HRID 2404236 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[CH3:16])=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2>O.C(O)(=O)C>[CH3:20][O:19][C:11]1[C:12]([O:17][CH3:18])=[CH:13][C:14]2[C:15]3[CH:16]=[N:1][NH:5][C:6]=3[CH:7]=[N:8][C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 612783HCID 612783, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 86686660HCID 86686660, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Sodium nitrite (1.28 g, 18.60 mmol), dissolved in water (2.5 ml), is added to a solution of 3-amino-6,7-dimethoxy-4-methylquinoline (2.70 g, 12.39 mmol) in glacial acetic acid (90 ml). The reaction mixture is stirred at room temperature for 3 h. When the reaction is complete, the mixture is evaporated in vacuo. The residue is taken up in water, filtered and rinsed with water. The filtrate is evaporated to dryness in vacuo. The residue obtained is filtered off with suction a number of times through a little flash silica gel in a frit with cyclohexane/ethyl acetate 4:1 (parts by volume) in order to remove impurities. The filtrate is discarded. The filter cake is subsequently washed with ethyl acetate/0-10% by vol. of ethanol, and the filtrate is evaporated to dryness in vacuo, giving 7,8-dimethoxy-3H-pyrazolo[3,4-c]-quinoline (2.29 g, purity 85%, 8.48 mmol) as a solid. MS: 230.0 (M+H+), TLC (HPTLC): Rf=0.45 (ethyl acetate/ethanol 8:1, parts by volume).

Workup

  1. customthe mixture is evaporated in vacuo
  2. filtrationfiltered
  3. washrinsed with water
  4. customThe filtrate is evaporated to dryness in vacuo
  5. customThe residue obtained
  6. filtrationis filtered off with suction a number of times through a little flash silica gel in a frit with cyclohexane/ethyl acetate 4:1 (parts by volume) in order
  7. customto remove impurities
  8. washThe filter cake is subsequently washed with ethyl acetate/0-10% by vol. of ethanol
  9. customthe filtrate is evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-2c4bc50c7e194a0ebfef436f9010100d
Source dataset
uspto-grants-2014_08
Patent number
US08802712B2

Reaction notes

Loading…