Hydrochloric Acid → N-(3-amino-4-chlorobenzyl)cyclopropanecarboxamide

HRID 59292Notes

Reaction equation

HRID 59292 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][NH:7][C:8]([CH:10]2[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[N+:15]([O-])=O.Cl>[Fe].CO>[NH2:15][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:2]=1[Cl:1])[CH2:6][NH:7][C:8]([CH:10]1[CH2:12][CH2:11]1)=[O:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 90019905N-(4-chloro-3-nitrobenzyl)cyclopropanecarboxamide

Product 1

HCID 89035202N-(3-amino-4-chlorobenzyl)cyclopropanecarboxamideYield 56.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared by following the procedure as described in step-2 of Intermediate-28 by using N-(4-chloro-3-nitrobenzyl)cyclopropanecarboxamide (0.400 g), methanol (10 mL), iron powder (catalytic) and conc. HCl (5 mL). The reaction mass was refluxed for 2 h. The reaction mass was quenched in water and basified with NaHCO3 and extracted with DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.200 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 0.65 (d, J=8.4 Hz, 4H), 1.57 (m, 1H), 4.11 (d, J=5.4 Hz, 2H), 5.34 (s, 2H), 6.41 (d, J=7.2 Hz, 1H), 7.10 (d, J=7.8 Hz, 1H), 8.50 (br s, 1H); MS (m/z): 225.07 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. temperatureThe reaction mass was refluxed for 2 h
  3. customThe reaction mass was quenched in water
  4. extractionextracted with DCM
  5. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6b05e51ffe3c46bc9f1bbfcdefa15fa3
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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