Methanol → HCID 18928646, compound

HRID 1599441Notes

Reaction equation

HRID 1599441 reaction equation
[C:1]1(=[O:12])[O:7][C:5](=O)[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1.[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17].CO>C1(C)C=CC=CC=1.C(Cl)Cl>[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][N:17]1[C:1](=[O:12])[CH2:2][C:3]2[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5]1=[O:7]

Participants

6

Reactant 3

HCID 887MethanolHCID 12801Homophthalic anhydrideHCID 666492-Fluorobenzylamine

Product 1

HCID 18928646HCID 18928646, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 800 mg (4.9 mmol) homophthalic anhydride, 680 mg (5.4 mmol) 2-fluorobenzylamine and 500 mg 4 Å molecular sieves in 1.5 mL toluene was stirred and heated at reflux overnight. A solution of 30% MeOH in CH2Cl2 was added, the resulting hot mixture filtered and the tiltrate concentrated to give 900 mg 2-(2-fluorobenzyl)-4H-isoquinoline-1,3-dione, mp 140°-144° C. A 500 mg (1.86 mmol) portion of this product was combined with 570 mg (3.71 mmol) DBU in 5 mL CH2Cl2 under argon, and cooled to -10° C. Isopropylsulfonyl chloride (290 mg, 2.04 mmol) was added, and after stirring 15 min the reaction was allowed to warm to room temperature. After 4 hr the reaction was diluted with EtOAc and worked up as in Example 1 giving 329 mg of the title compound, mp 174°-181° C.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. filtrationthe resulting hot mixture filtered
  4. concentrationthe tiltrate concentrated

Sources & evidence

ORD record
ord-9aecbf94213b4e76827515b4fa15c4fc
Source dataset
uspto-grants-1998_04
Patent number
US05741798

Reaction notes

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