HCID 65341729, compound → HCID 65343583, compound

HRID 1485383Notes

Reaction equation

HRID 1485383 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([NH:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:7]=1>[NH4+].[Cl-].C(O)C.[Fe]>[NH2:15][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[NH:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 1

HCID 65341729HCID 65341729, compound

Product 1

HCID 65343583HCID 65343583, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

Iron powder (7 g, 0.12 mol) was added to a mixture of methyl 3-(5-bromo-2-nitrophenylamino)propanoate (12 g, 0.04 mol) in aq. NH4Cl solution (50 mL) and ethanol (100 mL). After heating at 60° C. for 2 h, the mixture solution was filtered. The filtrate was evaporated, diluted with water (100 mL), extracted with ethyl acetate (150 mL), dried and concentrated to give the crude product, which was purified by CombiFlash to afford methyl 3-((2-amino-5-bromophenyl)amino)propanoate (9.4 g, yield 84%). LRMS (M+H)+: 272 m/z. 1H NMR (300 MHz, CDCl3) δ 2.67-2.72 (d, 2H, J=6.3 Hz), 3.40-3.44 (d, 2H, J=6.3 Hz), 3.72 (s, 3H), 4.58 (br, 3H), 6.67-6.70 (d, 2H, J=8.1 Hz), 6.80-6.82 (m, 2H).

Workup

  1. filtrationthe mixture solution was filtered
  2. customThe filtrate was evaporated
  3. additiondiluted with water (100 mL)
  4. extractionextracted with ethyl acetate (150 mL)
  5. customdried
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by CombiFlash

Sources & evidence

ORD record
ord-f311c8781c234234b33b6e70a95dc280
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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