Dimethylformamide → HCID 178483391, compound

HRID 2236733Notes

Reaction equation

HRID 2236733 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.[CH2:17]([N:19]([CH2:22][CH3:23])[CH2:20]C)C.C[N:25]([CH3:28])C=O>>[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:25][C:28]1[CH:6]=[CH:5][C:4]([CH2:9][CH2:23][CH2:22][N:19]([CH3:17])[CH3:20])=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178483391HCID 178483391, compoundYield 75%

Procedure

(4E)-6-Bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (50 mg, 0.18 mmol) 4-(3-dimethylamino-propyl)-phenylamine hydrochloride (0.40 mmol) were stirred in N,N-dimethylformamide (1 mL) and triethylamine (140 μL) at 78° C. The reaction mixture is quenched by the addition of water. The solid material is then collected, washed with water, and then dried under vacuum to give (4Z)-6-bromo-4-[({4-[3-(dimethylamino)propyl]phenyl}amino)methylene]isoquinoline-1,3(2H,4H)-dione (58 mg, 75%) as a golden solid.

Workup

  1. customat 78° C
  2. customThe reaction mixture is quenched by the addition of water
  3. customThe solid material is then collected
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ae8f4788fb82401285e601a6c62ce654
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…