Ammonia → HCID 54549569, compound

HRID 1508789Notes

Reaction equation

HRID 1508789 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([O:13]C)=O)=[CH:4][CH:3]=1.[Cl-].[NH4+:16].N>CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH2:16])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 88628Methyl 4-aminobenzenebutanoate

Product 1

HCID 54549569HCID 54549569, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A 100-mL vial was charged with methyl 4-(4-aminophenyl)butanoate (2.07 g, 10.7 mmol), ammonium chloride (0.76 g, 14.2 mmol) in methanol (10 mL). To this mixture was added NH3 (10 mL, 7N in methanol, 70.0 mmol, 6.5 eq.). The vial was sealed and the resulting mixture was stirred at 100° C. for 20 h. After this time, the crude reaction solution was concentrated under reduced pressure. The residue was absorbed on silica (10 g) then purified by chromatography on silica using dichloromethane/methanol (10:0 to 9:1) as eluent to afford the title compound (0.67 g, 35%) as a white solid. MW=178.23. 1H NMR (DMSO-d6, 500 MHz) δ 7.20 (br s, 1H), 6.83-6.80 (m, 2H), 6.66 (br s, 1H), 6.49-6.46 (m, 2H), 2.37 (t, J=7.5 Hz, 2H), 2.01 (t, J=7.5 Hz, 2H), 1.68 (quin, J=7.5 Hz, 2H).

Workup

  1. customThe vial was sealed
  2. customAfter this time, the crude reaction solution
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was absorbed on silica (10 g)
  5. customthen purified by chromatography on silica

Sources & evidence

ORD record
ord-4ae8fe2cdd62459e97ed0a250f40cefb
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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