Bromine → Methyl 2-amino-5-bromonicotinate

HRID 1825970

Reaction equation

HRID 1825970 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, 1 H), 8.23 (d, J=2.5 Hz, 1 H), 6.40 (br s, 2 H), 3.90 (s,3 H).

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-ddc0fbeadd5548688fa89a62a9b3dc10
Source dataset
uspto-grants-2006_05
Patent number
US07049310B2

Linked notes

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