Water → HCID 58532486, compound

HRID 75275Notes

Reaction equation

HRID 75275 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=O.[Br:6][C:7]1[CH:8]=[C:9]([N+:14]([O-:16])=[O:15])[C:10]([CH3:13])=[N:11][CH:12]=1.COC(OC)N(C)C.O>C(O)(C)C>[Br:6][C:7]1[CH:8]=[C:9]([N+:14]([O-:16])=[O:15])[C:10](/[CH:13]=[CH:3]/[N:2]([CH3:5])[CH3:1])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 250672665-Bromo-2-methyl-3-nitropyridine

Product 1

HCID 58532486HCID 58532486, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N,N-Dimethylformamide (270 kg), 5-bromo-2-methyl-3-nitropyridine (90.0 kg, 415 mol), and N,N-dimethylformamide dimethyl acetal (108.0 kg, 906.3 mol) were added to a 2000 L vessel at RT. The reaction mixture was stirred at RT for 30 minutes, then heated to 90±5° C. over a 3-hour period and maintained at this temperature for 4 hours. The mixture was subsequently cooled to 25±5° C. Water (945 kg) was added while keeping the temperature of the mixture at 25±5° C. After the addition of water, the reaction mixture was stirred for 2 hours. The solids were centrifuged to obtain wet product, which was slurried in isopropanol (207 kg) for 1 hour at 25±5° C. The solids were centrifuged again to obtain the title compound as a wet solid (105 kg, 92.5 wt % assay). The product was used in the next step without additional drying.

Workup

  1. temperatureheated to 90±5° C. over a 3-hour period
  2. temperaturemaintained at this temperature for 4 hours
  3. temperatureThe mixture was subsequently cooled to 25±5° C
  4. customat 25±5° C
  5. stirringthe reaction mixture was stirred for 2 hours
  6. customto obtain wet product, which

Sources & evidence

ORD record
ord-41498bbe4ddf4f38bb7d93548a99706d
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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