Stannous Chloride → HCID 67235894, compound

HRID 1748342Notes

Reaction equation

HRID 1748342 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 flask containing a solution of tin (II) chloride (1.1 g, 6 mmol) in concentrated HCl (1.5 mL) is added a solution of 4-chloro-2-(morpholin-4-ylmethyl)-6-nitroaniline (543 mg, 2 mmol) in concentrated HCl (1 mL). The reaction is stirred for 1 h. The thick slurry is filtered and the filter cake rinsed with HCl. The filter cake is dissolved in water (10 mL), is treated with 2M aqueous K2CO3 and is 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 water (10 mL)
  4. additionis treated with 2M aqueous K2CO3
  5. extractionis extracted with CH2Cl2
  6. customThe organic layer is separated
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-75c2d2bd90d84cc7bb207f5ecef27fe7
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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