Hexane → HCID 178518258, compound

HRID 2236603Notes

Reaction equation

HRID 2236603 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]/OC.[N:17]1([CH2:22][C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1.CCCCCC>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:27][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 7768524-(Pyrrolidin-1-ylmethyl)anilineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178518258HCID 178518258, compoundYield 106.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione, (0.15 g, 0.53 mmol) in N,N′-dimethylformamide is added 4-(pyrrolidinyl-methyl)aniline (0.10 mL, 0.58 mmol). The reaction mixture is heated at 120° C. under N2. Reaction is monitored by mass spectroscopy. After reaction is completed after 1.5 h. After evaporating the solvent, warm ethyl acetate is added to the residue to generate reddish orange residue. It is filtered through a pad of celite to give a yellow solution, which upon addition of hexane generated 0.24 g (62.8% yield) of orange solid: mp 165-166° C., Analysis for C21H20BrN3O2, Calcd: C, 59.17; H, 4.73; N, 9.86. Found: C, 58.77; H, 4.42; N, 9.81.

Workup

  1. customReaction
  2. customAfter reaction
  3. customAfter evaporating the solvent
  4. temperaturewarm ethyl acetate
  5. additionis added to the residue
  6. filtrationIt is filtered through a pad of celite
  7. customto give a yellow solution, which

Sources & evidence

ORD record
ord-3945ad72fcfb436ab247f6858ade963c
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…