Sodium Hydroxide → HCID 20570092, compound

HRID 1577857Notes

Reaction equation

HRID 1577857 reaction equation
[N+](C1C=CC(OCC(O)COC2C=CC([N+]([O-])=O)=CC=2)=CC=1)([O-])=O.NC1C=CC(OCC(O)COC2C=CC(N)=CC=2)=CC=1.C(OC=C(C(O)=O)C(O)=O)C.[C:56]([C:61]1[C:70](=[O:71])[C:69]2[C:64](=[CH:65][CH:66]=[C:67]([O:72][CH2:73][CH:74]([OH:93])[CH2:75][O:76][C:77]3[CH:78]=[C:79]4[C:84](=[CH:85][CH:86]=3)[NH:83][CH:82]=[C:81]([C:87]([O:89]CC)=[O:88])[C:80]4=[O:92])[CH:68]=2)[NH:63][CH:62]=1)([O:58]CC)=[O:57].[OH-].[Na+]>CO.[Pd].[C].O>[C:87]([C:81]1[C:80](=[O:92])[C:79]2[C:84](=[CH:85][CH:86]=[C:77]([O:76][CH2:75][CH:74]([OH:93])[CH2:73][O:72][C:67]3[CH:68]=[C:69]4[C:64](=[CH:65][CH:66]=3)[NH:63][CH:62]=[C:61]([C:56]([OH:58])=[O:57])[C:70]4=[O:71])[CH:78]=2)[NH:83][CH:82]=1)([OH:89])=[O:88]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 2128492-Propanol, 1,3-bis(p-aminophenoxy)-HCID 459027HCID 459027, compoundHCID 14715768(Ethoxymethylidene)propanedioic acidHCID 20570079HCID 20570079, compound

Product 1

HCID 20570092HCID 20570092, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

10 g. (30 mmol) of 1,3-bis(4-nitrophenoxy)-2-propanol is hydrogenated in methanol in the presence of 1.6 g. of Pd-carbon (10%). The catalyst is filtered off, and the filtrate is evaporated, leaving 13 g. of crude, oily 1,3-bis-(4-aminophenoxy)-2-propanol. This product is heated with 100 ml. of the diethyl ester of ethoxymethylenemalonic acid for 3 hours to 100°, then for 1 hour to 100° in a water jet pump vacuum. The excess diethyl ester of ethoxymethylenemalonic acid is distilled off under vacuum. The remainder is refluxed in 150 ml. of "Dowtherm A" for 30 minutes. After cooling, the solution is combined with isopropyl ether, and the thus-separated solid product is filtered off, thus obtaining 4 g. of crude 1,3-bis(3-carbethoxy-1,4-dihydro-4-oxo-6-quinolyloxy)-2-propanol, which is refluxed for 1 hour in 100 ml. of 2 N NaOH. After cooling, the mixture is extracted with ethyl acetate, and the aqueous phase is acidified with hydrochloric acid. The thus-produced oily compound is separated and stirred with ether until it has become solid. The solid product is filtered off, recrystallized from dimethylformamide, and dried under vacuum at 100°.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customleaving 13 g
  4. temperatureThis product is heated with 100 ml
  5. distillationThe excess diethyl ester of ethoxymethylenemalonic acid is distilled off under vacuum
  6. temperatureThe remainder is refluxed in 150 ml
  7. temperatureAfter cooling
  8. filtrationthe thus-separated solid product is filtered off
  9. customthus obtaining 4 g
  10. temperatureAfter cooling
  11. extractionthe mixture is extracted with ethyl acetate
  12. customThe thus-produced oily compound is separated
  13. filtrationThe solid product is filtered off
  14. customrecrystallized from dimethylformamide
  15. customdried under vacuum at 100°

Sources & evidence

ORD record
ord-8686faa7bef040d3a805c26fce2b91e1
Source dataset
uspto-grants-1981_09
Patent number
US04289777

Reaction notes

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