Bromine → 2-Amino-5-bromonicotinaldehyde hydrobromide

HRID 1362110Notes

Reaction equation

HRID 1362110 reaction equation
[Br:1]Br.[NH2:3][C:4]1[C:9]([CH:10]=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1>CC(O)=O>[BrH:1].[NH2:3][C:4]1[C:9]([CH:10]=[O:11])=[CH:8][C:7]([Br:1])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 866061462-Amino-5-bromonicotinaldehyde hydrobromideYield 156.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (1.1 mL, 20 mmol) in HOAc (20 mL) was added dropwise to a solution of 2-amino-pyridine-3-carbaldehyde (2.5 g, 20 mmol) in HOAc (50 mL) while stirring. After the addition, the mixture was allowed to stir for 2 h at room temperature. The precipitate was collected by filtration and washed with diethyl ether to afford the title compound (4.4 g, 77%) as a pale yellow solid: MS (ESI) m/e 201 (M+H)+.

Workup

  1. additionAfter the addition
  2. stirringto stir for 2 h at room temperature
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-ba7f4ab0eeae41a5a20858331f3db4bd
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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