Hydrogen Bromide → HCID 67280330, compound

HRID 1692640Notes

Reaction equation

HRID 1692640 reaction equation
N[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].Br.N([O-])=O.[Na+].[OH-:17].[Na+]>O>[CH3:11][C:7]1[C:3]2[C:4](=[O:5])[O:6][C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[O:17][C:2]=2[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 1512106-Methylanthranilic acidHCID 23668193Sodium Nitrite

Product 1

HCID 67280330HCID 67280330, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Cuprous bromide was added in one portion to a hot solution (90° C.) of 2-amino-6-methylbenzoic acid (10 g, 66 mmol) and HBr (26 mL, 40%) in H2O (160 ml). This was followed by the dropwise addition of a solution of NaNO2 (13.7 g, 198 mmol) in H2O (40 ml) over a period of 25 min. The reaction mixture was maintained at same temperature for 1 h and then was heated under reflux for another 0.5 h before it was cooled to room temperature and stirred for 2 h. Upon completion, the reaction mixture was carefully poured into ice water (1000 ml), and 5% NaOH solution was added until a pH of 14 was reached. The resulting suspension was filtered. The filtrate was acidified with diluted HCl to a pH of 1 and extracted with Et2O, Charcoal was added, and the resulting mixture was heated to reflux, filtered and evaporated by a rotatory evaporator to give a crude compound, which was recrystallized from Et2O/PE to afford the product (9.28 g, 65%).

Workup

  1. temperatureThe reaction mixture was maintained at same temperature for 1 h
  2. temperaturewas heated
  3. temperatureunder reflux for another 0.5 h before it
  4. additionwas added until a pH of 14
  5. filtrationThe resulting suspension was filtered
  6. extractionextracted with Et2O, Charcoal
  7. additionwas added
  8. temperaturethe resulting mixture was heated
  9. temperatureto reflux
  10. filtrationfiltered
  11. customevaporated by a rotatory evaporator
  12. customto give a crude compound, which
  13. customwas recrystallized from Et2O/PE

Sources & evidence

ORD record
ord-7cd5a9057d034c27a678aef90d328b65
Source dataset
uspto-grants-2012_04
Patent number
US08158623B2

Reaction notes

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