Hydrochloric Acid → HCID 57546000, compound

HRID 913880Notes

Reaction equation

HRID 913880 reaction equation
[NH2:1][C:2]1[C:9]([Br:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:3]=1[CH:4]=[O:5].Cl.N([O-])=O.[Na+].[N-:17]=[N+:18]=[N-].[Na+]>O>[N:1]([C:2]1[C:9]([Br:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:3]=1[CH:4]=[O:5])=[N+:17]=[N-:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 575461202-Amino-3-bromo-5-chlorobenzaldehyde

Product 1

HCID 57546000HCID 57546000, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a suspension of 2-amino-3-bromo-5-chlorobenzaldehyde (3.0 g, 12.8 mmol) in a water (4 mL) and hydrochloric acid (4 mL) mixture at 0° C. was added a solution of sodium nitrite (1.1 g, 16.0 mmol) in water (ca. 2 mL) dropwise. After 30 min, the ice bath was removed and the reaction stirred at room temperature for 30 min forming a white suspension. The solids were removed by filtration. The mother liquor was cooled to 0° C. and treated with sodium azide (0.8 g, 12.8 mmol) in water (2.0 mL). The ice bath was removed and stirring was continued for 30 min. The resulting solid was collected by filtration and dried in vacuo for several hours to afford 2.6 g (76%) as a white solid. 1H-NMR (CDCl3, 500 MHz) δ 10.30 (s, 1H), 7.78 (d, J=2.4 Hz, 1H), 7.77 (d, J=2.5 Hz, 1H).

Workup

  1. customthe ice bath was removed
  2. customforming a white suspension
  3. customThe solids were removed by filtration
  4. temperatureThe mother liquor was cooled to 0° C.
  5. customThe ice bath was removed
  6. stirringstirring
  7. waitwas continued for 30 min
  8. filtrationThe resulting solid was collected by filtration
  9. customdried in vacuo for several hours
  10. customto afford 2.6 g (76%) as a white solid

Sources & evidence

ORD record
ord-1419f819568a4bfabe2f9eb2214073e1
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

Loading…