Potassium Carbonate → HCID 65341729, compound

HRID 1485382Notes

Reaction equation

HRID 1485382 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.Cl.[NH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 65341729HCID 65341729, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-2-fluoro-1-nitrobenzene (10 g, 45.5 mol), methyl 3-aminopropanoate hydrochloride (6.4 g, 45.5 mol) and K2CO3 (19 g, 136.5 mol) in THF (250 mL) was heated at 100° C. for 4 hrs. The mixture was extracted with ethyl acetate (100 mL), washed with brine (150 mL), dried and concentrated to give the residue, which was purified by CombiFlash (PE:EA=2:1) to give methyl 3-((5-bromo-2-nitrophenyl)amino)propanoate (12 g, yield 88%). 1H NMR (300 MHz, CDCl3) δ 2.70-2.75 (t, J=6.6 Hz, 2H), 3.58-3.65 (m, 2H), 3.74 (s, 3H), 6.76-6.80 (m, 1H), 7.02-7.03 (d, J=2.1 Hz, 1H), 8.01-8.04 (d, J=9.0 Hz, 2H), 8.20-8.22 (br, 1H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (100 mL)
  2. washwashed with brine (150 mL)
  3. customdried
  4. concentrationconcentrated
  5. customto give the residue, which
  6. customwas purified by CombiFlash (PE:EA=2:1)

Sources & evidence

ORD record
ord-67ebf686fefd43d2b483d36964d6e16b
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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