Pyridine → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-dimethylaminocarbonyloxy-isoindolin-1-one

HRID 66336Notes

Reaction equation

HRID 66336 reaction equation
N1C=CC=CC=1.C(N(CC)CC)C.[CH3:14][N:15]([CH3:19])[C:16](Cl)=[O:17].[Cl:20][C:21]1[N:30]=[C:29]2[C:24]([CH:25]=[CH:26][C:27]([N:31]3[CH:39]([OH:40])[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:32]3=[O:41])=[N:28]2)=[CH:23][CH:22]=1>C(Cl)Cl.O>[Cl:20][C:21]1[N:30]=[C:29]2[C:24]([CH:25]=[CH:26][C:27]([N:31]3[CH:39]([O:40][C:16]([N:15]([CH3:19])[CH3:14])=[O:17])[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:32]3=[O:41])=[N:28]2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 199004082-(7-Chloro-1,8-naphthyridin-2-yl)-3-hydroxyisoindolin-1-one

Product 1

HCID 227547292-(7-Chloro-1,8-naphthyridin-2-yl)-3-dimethylaminocarbonyloxy-isoindolin-1-oneYield 73.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Pyridine (10 cc.), triethylamine (5 cc.) and dimethylcarbamoyl chloride (1.61 g.) are added successively to a suspension of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-isoindolin-1-one (3.11 g.) in methylene chloride (50 cc.). The reaction mixture is stirred for 16 hours at a temperature of about 20° C. and water (50 cc.) and methylene chloride (25 cc.) are then added. The aqueous layer is decanted off and washed with methylene chloride (2 × 25 cc.). The organic layers are combined, washed with water (2 × 25 cc.), dried over sodium sulphate and evaporated to dryness under reduced pressure. Recrystallisation of the residue obtained from acetonitrile (45 cc.) gives 2-(7-chloro-1,8-naphthyridin-2-yl)-3-dimethylaminocarbonyloxy-isoindolin-1-one (2.8 g.) melting at 218° C.

Workup

  1. additionare then added
  2. customThe aqueous layer is decanted off
  3. washwashed with methylene chloride (2 × 25 cc.)
  4. washwashed with water (2 × 25 cc.)
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness under reduced pressure
  7. customRecrystallisation of the residue
  8. customobtained from acetonitrile (45 cc.)

Sources & evidence

ORD record
ord-43a0c6e23a974922b33e781c8dadb8d1
Source dataset
uspto-grants-1978_12
Patent number
US04131674

Reaction notes

Loading…