Sodium Hydroxide → HCID 117702669, compound

HRID 873942Notes

Reaction equation

HRID 873942 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[C:5]([NH2:10])=[C:4]([CH3:11])[CH:3]=1.[N:12]([O-])=O.[Na+].[OH-].[Na+]>Cl.O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]2[N:10]=[N:12][N:8]([CH3:9])[C:6]=2[CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 69058379HCID 69058379, compound

Product 1

HCID 117702669HCID 117702669, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 5-bromo-N1,3-dimethylbenzene-1,2-diamine (Step 85.2) (2.5 g, 11.62 mmol) in HCl cc (15 mL, 494 mmol) cooled down to 0° C. was slowly added a solution of NaNO2 (0.962 g, 13.95 mmol) in water (25 mL). The resulting mixture was allowed to warm up and stir at RT for 2 hr. NaOH was added until basic pH, a precipitate occurred. The resulting solid was filtrated off, washed with water and dried under reduced pressure to afford the title product (2.5 g, 9.95 mmol, 86% yield) as beige solid. tR: 0.93 min (LC-MS 2); ESI-MS: 228 [M+H]+ (LC-MS 2).

Workup

  1. temperatureto warm up
  2. filtrationThe resulting solid was filtrated off
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-e69812a42aa540ab823d5ac776b6a3c9
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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