Methylamine → 6-bromo-N-methyl-2-naphtamide

HRID 1444940Notes

Reaction equation

HRID 1444940 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.S(Cl)(Cl)=O.CN.[CH2:21]([N:23](CC)CC)C>CO.O.CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:23][CH3:21])=[O:14])[CH:6]=[CH:5]2

Participants

9

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 45498526-Bromo-2-naphthalenecarboxylic acid

Product 1

HCID 218796286-bromo-N-methyl-2-naphtamideYield 80.3%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

4 Liters of ethyl acetate and 25 mL of DMF were added to 500 g (1.99 mol) of 6-bromo-2-naphthoic acid. 188 mL (2.61 mol, 1.3 eq) of thionyl chloride was added dropwise at 30° C. or lower. The mixture was stirred at 65° C. for 30 minutes. After cooled to 25° C., a mixture of 408 mL (3.93 mol, 2 eq) of a 40% solution of methylamine in methanol and 558 mL (4.01 mol, 2 eq) of triethylamine was added dropwise at 25° C. or lower. The mixture was stirred at 25° C. for 3 hours. 2.5 Liters of water was added dropwise at 25° C. or lower. Crystals were filtered, and washed successively with 1.25 liters of a mixed solution of methanol/water=1/4. Vacuum drying (50° C.) to a constant weight afforded 422 g of 6-bromo-N-methyl-2-naphthamide (yield 80%).

Workup

  1. temperatureAfter cooled to 25° C.
  2. additionwas added dropwise at 25° C.
  3. stirringThe mixture was stirred at 25° C. for 3 hours
  4. filtrationCrystals were filtered
  5. washwashed successively with 1.25 liters of a mixed solution of methanol/water=1/4
  6. customVacuum drying (50° C.) to a constant weight

Sources & evidence

ORD record
ord-632ef0e50f124f98b59e1c4c7f7fe3eb
Source dataset
uspto-grants-2010_02
Patent number
US07662974B2

Reaction notes

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