Propylene Oxide → HCID 613141, compound

HRID 1583805Notes

Reaction equation

HRID 1583805 reaction equation
[OH:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([N+:14]([O-:16])=[O:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:17][CH2:18][CH2:19]Br.C(N(CC)CC)C.C1OC1C>O.CN(C)P(=O)(N(C)C)N(C)C>[CH3:13][O:12][C:11]1[C:2]([O:1][CH2:17][CH2:18][CH3:19])=[C:3]2[C:8](=[C:9]([N+:14]([O-:16])=[O:15])[CH:10]=1)[N:7]=[CH:6][CH:5]=[CH:4]2

Participants

7

Reactant 4

HCID 6378Propylene OxideHCID 78401-BromopropaneHCID 8471TriethylamineHCID 1353992885323-58-0

Product 1

HCID 613141HCID 613141, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a stirred mixture of 15 g (0.068 mole) of 5-hydroxy-6-methoxy-8-nitroquinoline, 16.8 g (0.14 mole) of n-propyl bromide, 1.5 g of triethylamine and 20 g of hexamethylphosphoric triamide, heated at a bath temperature of 110°, was added dropwise, during 2 hr, 20 g of propylene oxide. After an additional 48 hr at 110° the green-brown mixture was poured into 150 ml of water. The aqueous mixture was extracted with diethyl ether and the extract was dried (magnesium sulfate) and concentrated to give a dark yellow residue. Crystallization from hexane provided 11.1 grams (62%) of 6-methoxy-8-nitro-5-(n-propoxy)quinoline as yellow crystals, mp 100°-104°. Recrystallization from methanol gave an analytical sample as pale yellow crystals, mp 101°-103°.

Workup

  1. temperatureheated at a bath temperature of 110°
  2. additionwas added dropwise, during 2 hr
  3. extractionThe aqueous mixture was extracted with diethyl ether
  4. dry with materialthe extract was dried (magnesium sulfate)
  5. concentrationconcentrated
  6. customto give a dark yellow residue
  7. customCrystallization from hexane

Sources & evidence

ORD record
ord-7fe2f3fd3b7844219d8d3c06840b8163
Source dataset
uspto-grants-1985_11
Patent number
US04554279

Reaction notes

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