4-(Quinolin-2-ylmethoxy)aniline → 4-(Quinolin-2-ylmethoxy)phenylhydrazine

HRID 33885Notes

Reaction equation

HRID 33885 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>[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 27475694-(Quinolin-2-ylmethoxy)anilineHCID 5352426Tin atomHCID 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 chlrodie (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-95238443306142f79127fd0dcfbeea54
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

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