Water → 2-n-Butyl-3,5-dihydro-5-phenyl-furo [3,2-c][1,8]naphthyridin-4(2H)-one

HRID 2118684Notes

Reaction equation

HRID 2118684 reaction equation
O[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[C:3]=1[CH2:19][CH:20]([OH:25])[CH2:21][CH2:22][CH2:23][CH3:24].O>Br>[CH2:21]([CH:20]1[O:25][C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[N:7][C:6]=3[N:5]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:4](=[O:18])[C:3]=2[CH2:19]1)[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 962WaterHCID 547178204-hydroxy-3-(2-hydroxyhexyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 139345872-n-Butyl-3,5-dihydro-5-phenyl-furo [3,2-c][1,8]naphthyridin-4(2H)-one

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-hydroxy-3-(2-hydroxyhexyl)-1-phenyl-1,8-naphthyridin-2(1H)-one (2g.) in 47% HBr was stirred in an atmosphere of nitrogen and heated to 80° C. for 41/2 hrs. after which time it was cooled and poured into water. The precipitate was filtered off, washed with water, dried in air, recrystallized from ethanol/charcoal to yield the product m.p. 179°-180° C.

Workup

  1. temperatureafter which time it was cooled
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried in air
  5. customrecrystallized from ethanol/charcoal

Sources & evidence

ORD record
ord-b0e9dd13a0bc4bd0b618966b6458f491
Source dataset
uspto-grants-1987_07
Patent number
US04680297

Reaction notes

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