Ethanolamine → Oracine

HRID 234978Notes

Reaction equation

HRID 234978 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:13]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:20](=[O:21])[C:12]=2[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:22].[NH2:23][CH2:24][CH2:25][OH:26].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:26][CH2:25][CH2:24][NH:23][CH2:2][CH2:3][N:4]1[C:13]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:20](=[O:21])[C:12]=2[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:22]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 10638655HCID 10638655, compound

Product 1

HCID 160047Oracine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1 g of 6-(2-chloroethyl)-5,11-dioxo-5,6-dihydro-11H-indeno[1,2-c]isoquinoline (IV, X=2, m.p. 214°-215° C.), 1 g of dry 2-aminoethanol and 1 g of anhydrous potassium carbonate in 30 ml of anhydrous dimethylformamide is treated by warming to 100°14 110° C. and kept at this temperature for two hours. The hot mixture is filtered and the product collected on filter washed with 10 ml of ethanol. After twelve hours of standing in refrigerator (5° C. the eliminated crystallic substance is separated by suction, washed with ethanol and dried at temperature of 60° C. The yield 0.7 g (65% of theory), m. p. of the product is 184° C. It is possible to purify the substance as in Example 1.

Workup

  1. additionis treated
  2. filtrationThe hot mixture is filtered
  3. customthe product collected
  4. filtrationon filter
  5. washwashed with 10 ml of ethanol
  6. waitAfter twelve hours of standing in refrigerator
  7. custom(5° C. the eliminated crystallic substance is separated by suction
  8. washwashed with ethanol
  9. customdried at temperature of 60° C
  10. customis 184° C
  11. customto purify the substance as in Example 1

Sources & evidence

ORD record
ord-bcf5efc5096c41329e22e8cd07d7d0af
Source dataset
uspto-grants-1997_01
Patent number
US05597831

Reaction notes

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