2-Bromopyridine-3-carboxylic acid → HCID 21525560, compound

HRID 1658765Notes

Reaction equation

HRID 1658765 reaction equation
Br[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:11][C:12]1[CH:17]=[C:16]([Br:18])[C:15]([Br:19])=[CH:14][C:13]=1[NH2:20]>>[Br:18][C:16]1[C:15]([Br:19])=[CH:14][C:13]2[NH:20][C:2]3[N:10]=[CH:9][CH:8]=[CH:7][C:3]=3[C:4](=[O:6])[NH:11][C:12]=2[CH:17]=1

Participants

3

Reactant 2

HCID 2332622-Bromopyridine-3-carboxylic acidHCID 121969444,5-Dibromobenzene-1,2-diamine

Product 1

HCID 21525560HCID 21525560, compound

Conditions

Temperature
150 °C

Procedure

A mixture of 0.1 mole of 2-bromonicotinic acid and 0.1 mole of 1,2-diamino-4,5-dibromobenzene is heated in an open vessel to 150° C. with vigorous stirring. After 3 minutes the source of heat is removed, and the reaction mixture is allowed to cool to room temperature and to crystallizes to give a solid. The solid is removed from the vessel, powdered, washed with dilute sodium hydroxide, and then with boiling water, and finally recrystallized from dioxane to give 6,11-dihydro-8,9-dibromo-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one.

Workup

  1. temperatureAfter 3 minutes the source of heat
  2. customis removed
  3. temperatureto cool to room temperature
  4. customto crystallizes
  5. customto give a solid
  6. customThe solid is removed from the vessel
  7. washwashed with dilute sodium hydroxide
  8. customwith boiling water, and finally recrystallized from dioxane

Sources & evidence

ORD record
ord-ddcf0b27ce1549f98633e31d806913d8
Source dataset
uspto-grants-1976_06
Patent number
US03966736

Reaction notes

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