3-Bromo-6-methoxychroman-4-one → HCID 20153986, compound

HRID 2414185Notes

Reaction equation

HRID 2414185 reaction equation
Br[CH:2]1[C:11](=O)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[O:4][CH2:3]1.[CH2:15]([NH:18][CH2:19][C:20](=[O:22])[CH3:21])[CH2:16][CH3:17]>C1(C)C=CC=CC=1.[N+](C)([O-])=O>[CH3:14][O:13][C:8]1[CH:7]=[CH:6][C:5]2[O:4][CH2:3][CH:2]3[N:18]([CH2:15][CH2:16][CH3:17])[CH2:19][C:20](=[O:22])[CH:21]=[C:11]3[C:10]=2[CH:9]=1

Participants

5

Reactant 2

HCID 123873073-Bromo-6-methoxychroman-4-oneHCID 201539561-(Propylamino)propan-2-one

Product 1

HCID 20153986HCID 20153986, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6375NitromethaneSolvent

Procedure

A mixture of 3-bromo-6-methoxy-4-chromanone (2.57 g) and 3.3 g of the ethylene ketal of 1-(propylamino)-2-propanone in 500 ml of toluene if refluxed for 17 hours. The resulting product is dissolved in 20 ml of nitromethane and added to 50 ml of 85% polyphosphoric acid. After 48 hours at room temperature the reaction is poured onto ice to afford 2,3,4a,5-tetrahydro-9-methoxy-4-propyl-4H-[1]-benzopyrano[3,4-b]pyridin-2-one.

Workup

  1. temperatureif refluxed for 17 hours
  2. additionAfter 48 hours at room temperature the reaction is poured onto ice

Sources & evidence

ORD record
ord-854c1836eb1845149729bfee3fc6cfeb
Source dataset
uspto-grants-1988_01
Patent number
US04721787

Reaction notes

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