(4E)-4-[(Dimethylamino)methylene]-1,4-dihydro-3(2H)-isoquinolinone → HCID 178517432, compound

HRID 2236583Notes

Reaction equation

HRID 2236583 reaction equation
C[N:2](/[CH:4]=[C:5]1/[C:6](=[O:15])[NH:7][CH2:8][C:9]2[C:14]/1=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:3].[NH:16]1[CH:20]=[C:19]([C:21]2[CH:27]=[CH:26]C(N)=[CH:23][CH:22]=2)[N:18]=[CH:17]1>C1(C)C=CC=CC=1>[NH:16]1[CH:20]=[C:19]([C:21]2[CH:27]=[CH:26][C:3]([NH:2]/[CH:4]=[C:5]3\[C:6](=[O:15])[NH:7][CH2:8][C:9]4[C:14]\3=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:23][CH:22]=2)[N:18]=[CH:17]1

Participants

4

Reactant 2

HCID 68694591(4E)-4-[(Dimethylamino)methylene]-1,4-dihydro-3(2H)-isoquinolinoneHCID 178507418HCID 178507418, compound

Product 1

HCID 178517432HCID 178517432, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A toluene (3 mL) solution containing (4E)-4-[(dimethylamino)methylene]-1,4-dihydro-3(2H)-isoquinolinone (300 mg, 1.48 mmol) and 4-(1H-imidazol-4-yl)aniline (265 mg, 1.66 mmol) is heated at 110° C. for 4 h. Using the same workup as example 1, 0.13 g (28%) orange solid is obtained: mp 151-152° C. (dec.); HRMS (ESI) m/z calcd for C19H16N4O 317.13969. found 317.13894 (M+H)+1.

Sources & evidence

ORD record
ord-1fe117cb5b84433cb6c1d42db61f50f8
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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