Water → 4-amino-3-chloro-N-(2-morpholin-4-ylethyl)benzamide

HRID 2234370Notes

Reaction equation

HRID 2234370 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[N+:19]([O-])=O)[C:5]([NH:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:6].[Cl-].[NH4+].O>C(O)C.C(O)(=O)C.[Fe]>[NH2:19][C:18]1[CH:17]=[CH:16][C:4]([C:5]([NH:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[O:6])=[CH:3][C:2]=1[Cl:1]

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 686820563-chloro-N-(2-morpholin-4-ylethyl)-4-nitro-benzamide2×

Product 1

HCID 643181314-amino-3-chloro-N-(2-morpholin-4-ylethyl)benzamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

3-chloro-N-(2-morpholin-4-ylethyl)-4-nitro-benzamide (Intermediate 53; 1.2 g, 3.82 mmol), iron powder (1.29 g, 22.95 mmol) and ammonium chloride (144 mg, 2.68 mmol) were heated in ethanol (27 mL) and water (9 mL at reflux for 1 h. A few drops of acetic acid were added and heating continued for a further 1 h. The reaction mixture was cooled, filtered and the filtrate concentrated. The residue was partitioned between DCM and sat NaHCO3. The organic layer was washed with brine, dried (MgSO4) and concentrated. Column chromatography of the residue gave the title compound as a white crystalline solid. (650 mg, 60%)

Workup

  1. temperatureheating
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. customThe residue was partitioned between DCM
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9a9806e02c694fd19dbcbc803490f3c3
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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