Ammonium Chloride → HCID 68468290, compound

HRID 1927742Notes

Reaction equation

HRID 1927742 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:29]=[CH:28][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][C:17]=3[F:27])=[C:13]([N+:30]([O-])=O)[CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[NH4+].[Cl-]>C1COCC1.C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[Zn]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:29]=[CH:28][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][C:17]=3[F:27])=[C:13]([NH2:30])[CH:12]=2)=[O:10])=[CH:33][CH:34]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 68467044Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)-2-nitrophenoxy)-3-fluorophenyl)acetate

Product 1

HCID 68468290HCID 68468290, compoundYield 99.3%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)-2-nitrophenoxy)-3-fluorophenyl)acetate (100 mg, 0.205 mmol) was diluted with THF (2 mL) followed by the addition of Zn dust (13.4 mg, 0.205 mmol) and saturated aq. NH4Cl (1 mL). After stirring for 1 hour, the reaction was diluted with ethyl acetate and 10% aq sodium carbonate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)-2-aminophenoxy)-3-fluorophenyl)acetate (93 mg, 99.1% yield).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8c9d1ec0acbb4b7ba33b8a4e46b55714
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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