Water → HCID 60631969, compound

HRID 1485390Notes

Reaction equation

HRID 1485390 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].F[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17].C([O-])([O-])=O.[K+].[K+].O>C1COCC1.C(OCC)(=O)C>[N+:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])([O-:18])=[O:17]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 2734767Methyl 3-aminopropanoate hydrochloride

Product 1

HCID 60631969HCID 60631969, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 3-aminopropanoate hydrochloride (15 g, 0.107 mol), 1-fluoro-2-nitrobenzene (14.9 g, 0.107 mol) and K2CO3 (36.6 g, 0.265 mol) in THF (50 mL) was heated at 90° C. and stirred overnight. After cooled to room temperature, water (20 mL) and ethyl acetate (40 mL) were added, and the separated organic layer was dried over Na2SO4, concentrated, and the resulting residue was purified by CombiFlash (PE:EA=4:1) to give methyl 3-((2-nitrophenyl)amino)propanoate (21.4 g, 90%). 1H NMR (300 MHz, CD3OD): δ 2.72 (t, J=6.6 Hz, 2H), 3.64-3.69 (m, 5H), 6.64-6.70 (m, 1H), 7.01-7.04 (m, 1H), 7.46-7.52 (m, 1H), 8.09-8.13 (m, 1H).

Workup

  1. temperatureAfter cooled to room temperature
  2. dry with materialthe separated organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customthe resulting residue was purified by CombiFlash (PE:EA=4:1)

Sources & evidence

ORD record
ord-c128f18c781f4857a9ab07913e2c3559
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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