Water → 7-benzyloxy-3-carboxy-6-methoxy-2-morpholino-4-(3,4,5-trimethoxyphenyl)-1(2H)isoquinolinone

HRID 1019369Notes

Reaction equation

HRID 1019369 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[C:18]2[C:12]([C:13]([C:23]3[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=3)=[C:14]([C:20]([OH:22])=[O:21])[O:15][C:16]2=O)=[CH:11][C:10]=1[O:35][CH3:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:37][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.C(Cl)(Cl)Cl.O>CN1CCN(C)C1=O>[CH2:1]([O:8][C:9]1[CH:19]=[C:18]2[C:12]([C:13]([C:23]3[CH:24]=[C:25]([O:33][CH3:34])[C:26]([O:31][CH3:32])=[C:27]([O:29][CH3:30])[CH:28]=3)=[C:14]([C:20]([OH:22])=[O:21])[N:37]([N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)[C:16]2=[O:15])=[CH:11][C:10]=1[O:35][CH3:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 20315N-AminomorpholineHCID 183989737-Benzyloxy-6-methoxy-4-(3,4,5-trimethoxyphenyl)isocoumarin-3-carboxylic acid

Product 1

HCID 183988087-benzyloxy-3-carboxy-6-methoxy-2-morpholino-4-(3,4,5-trimethoxyphenyl)-1(2H)isoquinolinone

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
100 °C

Procedure

7-Benzyloxy-6-methoxy-4-(3,4,5-trimethoxyphenyl)isocoumarin-3-carboxylic acid (5.0 g) and 4-aminomorpholine (6.2 g) are dissolved in 1,3-dimethyl-2-imidazolidinone (20 ml), and the mixture is heated at 100° C. with stirring overnight. To the reaction mixture are added chloroform and water. The chloroform layer is separated, washed, dried, and concentrated under reduced pressure to give 7-benzyloxy-3-carboxy-6-methoxy-2-morpholino-4-(3,4,5-trimethoxyphenyl)-1(2H)isoquinolinone. The product thus obtained is dissolved in dimethylformamide (15 ml), and thereto are added potassium carbonate (2.1 g) and methyl iodide (1.27 ml). The mixture is stirred at room temperature for 30 minutes, and thereto are added ethyl acetate and water. The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure. The residue is crystallized from diethyl ether to give 7-benzyloxy-6-methoxy-3-methoxycarbonyl-2-morpholino-4-(3,4,5-trimethoxyphenyl)-1(2H)isoquinolinone (3.4 g) as listed in Table 1.

Workup

  1. customThe chloroform layer is separated
  2. washwashed
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01c38d822071464b972fc2b87e148693
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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