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

HRID 724202Notes

Reaction equation

HRID 724202 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.Cl.[CH2:16]([N:18]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.CN>CN(C)C=O.C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:18][CH3:16])=[O:14])[CH:6]=[CH:5]2

Participants

9

Reactant 5

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 45498526-Bromo-2-naphthalenecarboxylic acid

Product 1

HCID 218796286-bromo-N-methyl-2-naphtamideYield 95.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-Bromo-2-naphthoic acid (60.26 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (55.21 g) and 1-hydroxy-1H-benzotriazole monohydrate (44.1 g) were dissolved in dimethylformamide (960 ml) under an argon atmosphere. N-Ethyldiisopropylamine (37.23 g) was added with stirring under ice-cooling. A solution (2M; 192 ml) of methylamine in THF was added and the mixture was stirred at room temperature for 18 h. The reaction mixture was poured into water (8 L) with stirring and the precipitate was collected by filtration. The precipitate was washed successively with water and diisopropyl ether, and dried in the presence of phosphorus pentaoxide at 70° C. to give the title compound (60.6 g) as a crystalline powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 18 h
  3. stirringwith stirring
  4. filtrationthe precipitate was collected by filtration
  5. washThe precipitate was washed successively with water and diisopropyl ether
  6. dry with materialdried in the presence of phosphorus pentaoxide at 70° C.

Sources & evidence

ORD record
ord-4d3f1c0be4c248248a53381ce6b49229
Source dataset
uspto-grants-2006_11
Patent number
US07141598B2

Reaction notes

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