Bromine → Methyl 2-amino-5-bromonicotinate

HRID 1361973Notes

Reaction equation

HRID 1361973 reaction equation
[Br:1]Br.[NH2:3][C:4]1[N:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]>CC(O)=O>[NH2:3][C:4]1[N:13]=[CH:12][C:11]([Br:1])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 24408BromineHCID 351633Methyl 2-aminopyridine-3-carboxylate

Product 1

HCID 2763453Methyl 2-amino-5-bromonicotinateYield 98.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (0.7 mL, 14 mmole) was added dropwise to a stirred solution of methyl 2-aminonicotinate (2.0 g, 13 mmole) in HOAc (50 mL). A suspension formed within 30 min. The reaction was allowed to stir at room temperature for 2 h, then was concentrated under vacuum. The residue was triturated with 1.0 N Na2CO3 (50 mL) and the solid was collected by suction filtration. The solid was washed with H2O (50 mL) and dried under vacuum to give the title compound (2.95 g, 98%) as a pale yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.24 (d, J=2.5 Hz, 1H), 8.23 (d, J=2.5 Hz, 1H), 6.40 (br s, 2H), 3.90 (s, 3H).

Workup

  1. customA suspension formed within 30 min
  2. concentrationwas concentrated under vacuum
  3. customThe residue was triturated with 1.0 N Na2CO3 (50 mL)
  4. filtrationthe solid was collected by suction filtration
  5. washThe solid was washed with H2O (50 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-09e8d2d259f3418ca2ff14e7577761ff
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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