Tin tetrachloride → 4-(Quinolin-2-ylmethoxy)phenylhydrazine

HRID 1170324Notes

Reaction equation

HRID 1170324 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1.[N:20]([O-])=O.[Na+].[Sn](Cl)(Cl)(Cl)Cl>Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][NH2:20])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 27475694-(Quinolin-2-ylmethoxy)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 152250684-(Quinolin-2-ylmethoxy)phenylhydrazine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a suspension of 4-(Quinolin-2-ylmethoxy)-phenylamine (1.73 g) in 30 mL of concentrated HCl at 0° C. was added sodium nitrite (531 mg). After 3 h, tin chloride (3.95 g) was dissolved in 20 mL of concentrated HCl and added slowly dropwise and the reaction mixture stirred at ambient temperature for 18 h. The reaction mixture was filtered and the solid dried to provide the title compound as the HCL salt (3.94 g). MS: (M+H m/z=266.3).

Workup

  1. additionadded slowly dropwise
  2. filtrationThe reaction mixture was filtered
  3. customthe solid dried

Sources & evidence

ORD record
ord-99d9de4731bf43bcaa981cb4efa95c16
Source dataset
uspto-grants-2010_11
Patent number
US07825254B2

Reaction notes

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