Water → HCID 15027720, compound

HRID 345963Notes

Reaction equation

HRID 345963 reaction equation
[NH2:1][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:7](=[O:15])[N:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])[C:5]=2[S:4][C:3]=1[C:23]([O:25][CH3:26])=[O:24].P(Cl)(Cl)(Cl)=O.O.C(=O)(O)[O-].[Na+].[CH3:38][N:39]1[CH2:43][CH2:42][CH2:41][C:40]1=O>>[CH3:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:6]1[C:5]2[S:4][C:3]([C:23]([O:25][CH3:26])=[O:24])=[C:2]([N:1]=[C:40]3[CH2:41][CH2:42][CH2:43][N:39]3[CH3:38])[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]1=[O:15]

Participants

6

Reactant 5

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 15027713HCID 15027713, compound

Product 1

HCID 15027720HCID 15027720, compound

Procedure

To a solution of methyl 1-amino-4,5-dihydro-4-(2-methylphenyl)-5-oxo-thieno[2,3-c]isoquinoline-2-carboxylate [M.P. 236°-237° C.), 510 mg] in 5 ml of N-methyl-2-pyrrolidone, which was prepared by a similar manner to that described in Example 2, was added 1.57 ml of phosphorus oxychloride at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was poured into 50 ml of water, and neutralized with a saturated sodium bicarbonate aqueous solution. Precipitates were collected by a filtration, washed with water, extracted with chloroform, and dried over anhydrous magnesium sulfate. The solution was evaporated under reduced pressure, and the residue was dried under reduced pressure to obtain 583 mg of the desired product as yellow crystals.

Workup

  1. customPrecipitates
  2. filtrationwere collected by a filtration
  3. washwashed with water
  4. extractionextracted with chloroform
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solution was evaporated under reduced pressure
  7. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-9dd18cd0db764a618dcd0fdff0be98db
Source dataset
uspto-grants-1991_10
Patent number
US05059692

Reaction notes

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