Sodium Hydroxide → HCID 20570092、化合物

HRID 1577857ノート

反応式

HRID 1577857 の反応式
[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]

参加物

9

反応物 5

HCID 14798Sodium HydroxideHCID 2128492-Propanol, 1,3-bis(p-aminophenoxy)-HCID 4590272-Propanol, 1,3-bis(p-nitrophenoxy)-HCID 14715768(Ethoxymethylidene)propanedioic acidHCID 20570079HCID 20570079、化合物

生成物 1

HCID 20570092HCID 20570092、化合物

試薬・触媒・溶媒 3

HCID 178418390HCID 178418390、化合物触媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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°.

後処理

  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°

出典と根拠

ORDレコード
ord-8686faa7bef040d3a805c26fce2b91e1
出典データセット
uspto-grants-1981_09
特許番号
US04289777

反応ノート

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