Ammonium Chloride → HCID 68468290, compound

HRID 453511Notes

Reaction equation

HRID 453511 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-ffee09a6593544faabc32a16e805abdf
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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