Water → 4-chloro-7,7-dimethyl-2',3',5',6',7,8-hexahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3,9(6H)-dione

HRID 573792Notes

Reaction equation

HRID 573792 reaction equation
O[C:2]1[C:11]2[C:12](=[O:20])[O:13][C:14]3([CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:10]=2[C:9]2[C:8](=[O:21])[CH2:7][C:6]([CH3:23])([CH3:22])[CH2:5][C:4]=2[N:3]=1.O.O=P(Cl)(Cl)[Cl:27]>CN(C)C=O>[Cl:27][C:2]1[C:11]2[C:12](=[O:20])[O:13][C:14]3([CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:10]=2[C:9]2[C:8](=[O:21])[CH2:7][C:6]([CH3:23])([CH3:22])[CH2:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 1784267954-Hydroxy-7,7-dimethyl-2',3',5',6',7,8-hexahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3,9(6H)-dione

Product 1

HCID 866625334-chloro-7,7-dimethyl-2',3',5',6',7,8-hexahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3,9(6H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

6.2 g 4-Hydroxy-7,7-dimethyl-2′,3′,5′,6′,7,8-hexahydro-3H-spiro[furo[3,4-c]quinoline-1,4′-pyran]-3,9(6H)-dione are suspended in 25 ml phosphoroxychloride, 1 drop of N,N-dimethylformamide is added and the mixture is heated for 18 hours to 65° C. Under vigorous stirring the mixture is added dropwise to 300 ml water while keeping the temperature below 35° C. After completion of the addition the mixture is stirred for 1 hour, the product is isolated by filtration, washed with water and dried in vacuo.

Workup

  1. temperaturethe mixture is heated for 18 hours to 65° C
  2. customthe temperature below 35° C
  3. additionAfter completion of the addition the mixture
  4. stirringis stirred for 1 hour
  5. customthe product is isolated by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-54851df2920c482ba7c6e02cd098c923
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

Loading…