Citric Acid → 5-naphthalen-1-yl-1H-pyrrole-2-carboxylic acid chloride

HRID 985608노트

반응식

HRID 985608 반응식
C[O:2][C:3]([C:5]1[NH:6][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)=O.O.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(Cl)(=O)C([Cl:39])=O>O1CCOCC1.O.CN(C=O)C>[C:10]1([C:7]2[NH:6][C:5]([C:3]([Cl:39])=[O:2])=[CH:9][CH:8]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

참가 물질

7

반응물 4

HCID 311Citric AcidHCID 65578Oxalyl chlorideHCID 168937Lithium hydroxide, monohydrateHCID 697453065-naphthalen-1-yl-1H-pyrrole-2-carboxylic acid methyl ester

생성물 1

HCID 879770875-naphthalen-1-yl-1H-pyrrole-2-carboxylic acid chloride

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

5-Naphthalen-1-yl-1H-pyrrole-2-carboxylic acid methyl ester was diluted with 1:1 dioxane-water (30 ml), and treated with lithium hydroxide hydrate (24.4 mmol, 1.02 g), then heated to reflux for 15 min. The solution was acidified with 20% aqueous citric acid (30 ml), then extracted with ethyl acetate (75 ml). The organics were washed with brine (2×20 ml), then concentrated under reduced pressure. The residue was diluted with CH2Cl2, (30 ml), and treated with oxalyl chloride (24.0 mmol, 2.10 ml), and DMF (one drop), then heated to reflux for 30 min. The solution was concentrated under reduced pressure to provide 1.95 g of 5-naphthalen-1-yl-1H-pyrrole-2-carboxylic acid chloride.

후처리

  1. temperatureheated
  2. temperatureto reflux for 15 min
  3. extractionextracted with ethyl acetate (75 ml)
  4. washThe organics were washed with brine (2×20 ml)
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue was diluted with CH2Cl2, (30 ml)
  7. temperatureheated
  8. temperatureto reflux for 30 min
  9. concentrationThe solution was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-478997a75ce0418794edde9dbb1412d2
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06872745B2

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