HCID 68326720, compound → HCID 68326404, compound

HRID 2274016Notes

Reaction equation

HRID 2274016 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:3]=1[C:4]([NH:6][C:7]1([C:10]#[N:11])[CH2:9][CH2:8]1)=[O:5]>C(OCC)(=O)C.C(O)(=O)C.[Fe]>[NH2:16][C:13]1[CH:14]=[CH:15][C:2]([Cl:1])=[C:3]([CH:12]=1)[C:4]([NH:6][C:7]1([C:10]#[N:11])[CH2:9][CH2:8]1)=[O:5]

Participants

5

Reactant 1

HCID 68326720HCID 68326720, compound

Product 1

HCID 68326404HCID 68326404, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

3.15 g of iron powder are suspended in 18 ml of 5% strength acetic acid, and a solution of 3.0 g of 2-chloro-N-(1-cyanocyclopropyl)-5-nitrobenzamide in a mixture of 25 ml of ethyl acetate and 22.6 ml of glacial acetic acid is added. During the addition, the internal temperature is kept below 45° C. The reaction mixture is stirred at room temperature for 14 hours and then filtered through Celite. The filtrate is diluted with water, and the aqueous phase is extracted three times with ethyl acetate. The combined organic phases are washed twice with a saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated on a rotary evaporator under reduced pressure. The crude product is triturated with a mixture of three parts of cyclohexane and one part of ethyl acetate, and the solid is filtered off. This gives 2.0 g (71%) of 5-amino-2-chloro-N-(1-cyanocyclopropyl)benzamide.

Workup

  1. additionis added
  2. additionDuring the addition
  3. customis kept below 45° C
  4. filtrationfiltered through Celite
  5. additionThe filtrate is diluted with water
  6. extractionthe aqueous phase is extracted three times with ethyl acetate
  7. washThe combined organic phases are washed twice with a saturated sodium chloride solution
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated on a rotary evaporator under reduced pressure
  11. customThe crude product is triturated with a mixture of three parts of cyclohexane and one part of ethyl acetate
  12. filtrationthe solid is filtered off

Sources & evidence

ORD record
ord-8488090b64524a43b45d2291abd6eebd
Source dataset
uspto-grants-2015_09
Patent number
US09126945B2

Reaction notes

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