Stannous Chloride → HCID 57770617, compound

HRID 2092622Notes

Reaction equation

HRID 2092622 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH:12]=[C:13]([NH2:15])[CH:14]=1)=[O:8])[CH3:5].[N:23]([O-])=O.[Na+].Cl[Sn]Cl>Cl.O>[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[CH:12]=[C:13]([NH:15][NH2:23])[CH:14]=1)=[O:8])[CH3:5]

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 23668193Sodium NitriteHCID 595997035-Amino-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

Product 1

HCID 57770617HCID 57770617, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

5-Amino-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (596 mg, 2 mmol) was dissolved in 6 mL of concentrated HCl and stirred for 15 minutes at 0° C. To the reaction mixture was added a solution of NaNO2 (138 mg, 2 mmol) in water (1.5 mL) dropwise at 0° C. The mixture was stirred for 30 minutes, and then a solution of SnCl2 (4.5 mmol, 189.6 mg) in 2 mL of concentrated HCl was added dropwise. A precipitate began to form immediately. After stirring for another 30 minutes, the resulting 5-hydrazino-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide was isolated as a hydrochloride salt by filtration and immediately used in the next step.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. customto form immediately
  3. stirringAfter stirring for another 30 minutes

Sources & evidence

ORD record
ord-36281800c5c14e2bbac64d5b027674e8
Source dataset
uspto-grants-2013_05
Patent number
US08440708B2

Reaction notes

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