Acetyl chloride → HCID 178475407, compound

HRID 2236600Notes

Reaction equation

HRID 2236600 reaction equation
BrC1C=C2C(=CC=1)C=NC/C/2=C\NCC1C=C[CH:18]=[C:17]([OH:21])C=1.[OH:22][C:23]1[CH:24]=[C:25]([CH:41]=[CH:42][C:43]=1[OH:44])[CH2:26][NH:27][CH:28]=[C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](=[O:39])[NH:31][C:30]1=[O:40].C(N(CC)CC)C.[C:52](Cl)(=[O:54])[CH3:53]>N1C=CC=CC=1>[C:52]([O:44][C:43]1[CH:42]=[CH:41][C:25]([CH2:26][NH:27]/[CH:28]=[C:29]2\[C:30](=[O:40])[NH:31][C:32](=[O:39])[C:33]3[C:38]\2=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:24][C:23]=1[O:22][C:17](=[O:21])[CH3:18])(=[O:54])[CH3:53]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86619579HCID 86619579, compoundHCID 178518332HCID 178518332, compound

Product 1

HCID 178475407HCID 178475407, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4Z)-4-{[(3,4-dihydroxybenzyl)amino]methylene}-isoquinoline-1,3(2H,4H)-dione, (0.2 g, 0.644 mmol) in 0.27 mL (1.93 mmol) of triethylamine and 5 mL of pyridine is stirred at room temperature for 10 min, then 0.1 mL (1.42 mmol) of acetyl chloride is added. The reaction mixture is stirred at room temperature under N2 for 3 h. After evaporating the solvent, the residue is dissolved in dichloromethane, washed twice with water, dried over Mg2SO4, filtered and concentrated to give yellow solid. Recrystallized in EtOAc/Hex to afford 0.28 g (65.1% yield) of light yellow solid: mp 184-186° C.; MS (ESI) m/z 395.3 (M+H)+1, Analysis for C21H18N2O6. Calcd: C, 63.96; H, 4.60; N, 7.10. Found: C, 63.56; H, 4.69; N, 6.72.

Workup

  1. customAfter evaporating the solvent
  2. dissolutionthe residue is dissolved in dichloromethane
  3. washwashed twice with water
  4. dry with materialdried over Mg2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give yellow solid
  8. customRecrystallized in EtOAc/Hex
  9. customto afford 0.28 g (65.1% yield) of light yellow solid

Sources & evidence

ORD record
ord-41e89277a6764b4fb4607aab1dc04844
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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