4-(Dimethylamino)benzoic acid → HCID 59374991, compound

HRID 661876Notes

Reaction equation

HRID 661876 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.ClC(N(C)C)=C(C)C.[Br:21][C:22]1[C:23]([CH3:29])=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25].CCN(C(C)C)C(C)C>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:21][C:22]1[C:23]([CH3:29])=[C:24]([NH:25][C:7](=[O:9])[C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:12])=[CH:11][CH:10]=2)[CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 120924-(Dimethylamino)benzoic acidHCID 81531DiisopropylethylamineHCID 1235383-Bromo-o-toluidineHCID 6407921-Chloro-N,N-2-trimethylpropenylamine

Product 1

HCID 59374991HCID 59374991, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A suspension of 4-(dimethylamino)benzoic acid (100 mg, 0.605 mmol) in DCM (3 mL) was treated with 1-chloro-N,N,2-trimethylprop-1-en-1-amine (0.120 mL, 0.908 mmol) and the resulting solution was stirred at rt for 1.5 h. 3-Bromo-2-methylaniline (0.053 mL, 0.432 mmol) was added, followed by DIEA (0.264 mL, 1.513 mmol). The mixture was stirred at rt for 1 h, then was diluted with DCM and NaHCO3 (aq). The layers were separated and the organic phase was washed with brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 85:15 to 65:35 hexane-EtOAc) to provide N-(3-bromo-2-methylphenyl)-4-(dimethylamino)benzamide as a light yellow solid (77 mg, 53%). 1H NMR (400 MHz, DMSO-d6) δ 9.75 (s, 1H) 7.85 (d, J=9.0 Hz, 2H) 7.49 (dd, J=8.0, 1.0 Hz, 1H) 7.30 (dd, J=7.9, 0.9 Hz, 1H) 7.15 (t, J=7.9 Hz, 1H) 6.75 (d, J=9.0 Hz, 2H) 2.99 (s, 6H) 2.25 (s, 3H). Mass spectrum m/z 331, 333 (M−H)−.

Workup

  1. stirringThe mixture was stirred at rt for 1 h
  2. customThe layers were separated
  3. washthe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (
  7. washeluting with a gradient from 85:15 to 65:35 hexane-EtOAc)

Sources & evidence

ORD record
ord-c1c2a567dc9a4133a0a177ac040826e4
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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