Stannous Chloride → HCID 67235894, compound

HRID 1521741Notes

Reaction equation

HRID 1521741 reaction equation
[Sn](Cl)Cl.[Cl:4][C:5]1[CH:11]=[C:10]([N+:12]([O-])=O)[C:8]([NH2:9])=[C:7]([CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:6]=1>Cl>[Cl:4][C:5]1[CH:11]=[C:10]([NH2:12])[C:8]([NH2:9])=[C:7]([CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:6]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 67235137HCID 67235137, compound

Product 1

HCID 67235894HCID 67235894, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a solution of tin (II) chloride (1.1 g, 6 mmol) in concentrated HCl (1.5 mL) is added 4-chloro-2-(morpholin-4-ylmethyl)-6-nitroaniline (543 mg, 2 mmol) as a solution in concentrated HCl (1 mL). The reaction is stirred for 1 hour. The thick slurry is filtered and the filter cake rinsed with HCl. The filter cake is dissolved in H2O (10 mL) and treated with 2M aqueous K2CO3 and extracted with CH2Cl2. The organic layer is separated, dried (Na2SO4) and concentrated to afford the title compound (458 mg, 95%) as an oil.

Workup

  1. filtrationThe thick slurry is filtered
  2. washthe filter cake rinsed with HCl
  3. dissolutionThe filter cake is dissolved in H2O (10 mL)
  4. additiontreated with 2M aqueous K2CO3
  5. extractionextracted with CH2Cl2
  6. customThe organic layer is separated
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d9a3cdda717646d793a0b3bd2966c050
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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