Ammonium Chloride → HCID 68466596, compound

HRID 1927711Notes

Reaction equation

HRID 1927711 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:13]=[CH:14][C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].[Zn]>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][C:15]2[CH:14]=[CH:13][C:12]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:11][C:10]=2[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:22][CH:21]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 68464706HCID 68464706, compound

Product 1

HCID 68466596HCID 68466596, compoundYield 100.2%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Methyl 2-(3-((tert-butoxycarbonyl)aminomethyl)-4-(4-nitrophenoxy)phenyl)acetate (242 mg, 0.581 mmol) was diluted with THF (3 mL) followed by the addition of Zn dust (38.0 mg, 0.581 mmol). About 2 mL of saturated ammonium chloride was added dropwise. After stirring the reaction for 10 minutes, the reaction mixture was diluted with ethyl acetate and saturated sodium bicarbonate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield 225 mg of methyl 2-(4-(4-aminophenoxy)-3-((tert-butoxycarbonyl)aminomethyl)phenyl)acetate.

Workup

  1. customthe reaction for 10 minutes
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8310c631adae4ea38a20b0f613116da2
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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