Stannous chloride dihydrate → 4-(8-benzyloxy-7-methoxy-3H-pyrazolo[3,4-c]quinolin-1-yl)benzonitrile

HRID 2404231Notes

Reaction equation

HRID 2404231 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[C:16]([C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1)=O)=[CH:13][C:12]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[C:11]([O:34][CH3:35])[CH:10]=2.O.O.[Sn](Cl)Cl>O.Cl>[CH2:27]([O:26][C:12]1[C:11]([O:34][CH3:35])=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:5][N:1]=[C:16]([C:18]4[CH:19]=[CH:20][C:21]([C:22]#[N:23])=[CH:24][CH:25]=4)[C:15]=3[C:14]=2[CH:13]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 23668193Sodium NitriteHCID 666325404-(3-Amino-6-benzyloxy-7-methoxyquinoline-4-carbonyl)benzonitrile

Product 1

HCID 666325304-(8-benzyloxy-7-methoxy-3H-pyrazolo[3,4-c]quinolin-1-yl)benzonitrileYield 93.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (483 mg, 6.99 mmol) in water (2.5 ml) is added dropwise over the course of 1.5 h at (−)1-0° C. to a suspension of 4-(3-amino-6-benzyloxy-7-methoxy-quinoline-4-carbonyl)benzonitrile (2.60 g, 6.35 mmol) in concentrated hydrochloric acid (50 ml). The mixture is subsequently stirred for a further 30 min. A solution of tin(II) chloride dihydrate (5.02 g, 22.23 mmol) in concentrated hydrochloric acid (3.8 ml) is then added at (−)5° C. The suspension obtained is stirred at room temperature for 1 h, subsequently diluted with water (500 ml), stirred for 30 min and filtered with suction. The filter cake is rinsed with water and dried in a high vacuum, giving 4-(8-benzyloxy-7-methoxy-3H-pyrazolo[3,4-c]quinolin-1-yl)benzonitrile (2.42 g, 5.95 mmol) as a solid having a melting point of 222.8° C. (decomposition). MS: 407.1 (M+H+), TLC (HPTLC): Rf=0.27 (ethyl acetate).

Workup

  1. customThe suspension obtained
  2. stirringis stirred at room temperature for 1 h
  3. stirringstirred for 30 min
  4. filtrationfiltered with suction
  5. washThe filter cake is rinsed with water
  6. customdried in a high vacuum

Sources & evidence

ORD record
ord-d8bfab2d30604f9c8675a84f48bb46dd
Source dataset
uspto-grants-2014_08
Patent number
US08802712B2

Reaction notes

Loading…