Ammonium Chloride → Ethyl (5-(4-(((3-amino-2-methylphenyl)(2-fluorobenzyl)amino)methyl)phenoxy)-2-chlorophenoxy)acetate

HRID 1370974Notes

Reaction equation

HRID 1370974 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[F:41])[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-])=O)[C:25]=3[CH3:33])=[CH:18][CH:17]=2)=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[NH4+].[Cl-]>C(O)C.O.[Fe]>[NH2:30][C:26]1[C:25]([CH3:33])=[C:24]([N:23]([CH2:22][C:19]2[CH:20]=[CH:21][C:16]([O:15][C:12]3[CH:13]=[CH:14][C:2]([Cl:1])=[C:3]([CH:11]=3)[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:17][CH:18]=2)[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[F:41])[CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86586239Ethyl (2-chloro-5-(4-(((2-fluorobenzyl)(2-methyl-3-nitrophenyl)amino)methyl)phenoxy)phenoxy)acetate

Product 1

HCID 86586238Ethyl (5-(4-(((3-amino-2-methylphenyl)(2-fluorobenzyl)amino)methyl)phenoxy)-2-chlorophenoxy)acetate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The product from Example 306B in ethanol (1.2 mL) and H2O (0.6 mL) was treated with iron powder (100 mg, 1.8 mmoles) and NH4Cl (10 mg, 0.18 mmoles) at 80° C. overnight. The reaction mixture filtered, residue washed with methanol and dichloromethane, the filtrate concentrated in vacuo to provide the title compound.

Workup

  1. filtrationThe reaction mixture filtered
  2. washresidue washed with methanol and dichloromethane
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-44c73b0a704e4a60b723d35f2ea9c38d
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

Loading…