Bromine → HCID 178465837, compound

HRID 128613Notes

Reaction equation

HRID 128613 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[N:12][C:13]=1[CH3:14])[N:10]=[CH:9][CH:8]=[C:7]2[OH:15])[CH3:2].[Br:16]Br>C(O)(=O)C.S(=O)(O)[O-].[Na+]>[Br:16][C:8]1[CH:9]=[N:10][C:11]2[C:6]([C:7]=1[OH:15])=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[C:13]([CH3:14])[N:12]=2

Participants

5

Reactant 2

HCID 24408BromineHCID 178465839HCID 178465839, compound

Product 1

HCID 178465837HCID 178465837, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 23665763Sodium BisulfiteSolvent

Procedure

A mixture of 6-ethoxy-7-methyl-1,8-naphthyridin-4-ol, (5.0 g) in glacial acetic acid (60 ml) was stirred at between 15°-20° C. while a solution of bromine (2.4 ml) in glacial acetic acid (10 ml) was added dropwise over 10 minutes. The mixture was stirred at ambient temperature for 1.5 hours and then filtered. The residue was washed with water, ground up in water and the mixture basified with sodium bicarbonate and filtered. The solid obtained was ground in sodium bisulphite solution and filtered to give 3-bromo-6-ethoxy-7-methyl-1,8-naphthyridin-4-ol, m.p. 266°-267° C.

Workup

  1. additionwas added dropwise over 10 minutes
  2. filtrationfiltered
  3. washThe residue was washed with water
  4. filtrationfiltered
  5. customThe solid obtained
  6. filtrationfiltered

Sources & evidence

ORD record
ord-1c353db1144a49c59c0aedd46bd69e4f
Source dataset
uspto-grants-1995_11
Patent number
US05464781

Reaction notes

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