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Acetic Acid → n-Propyl 2-amino-1,4-dihydro-5-cyano-6-methyl-4-(3-phenylquinolin-5-yl)-pyridine-3-carboxylate

HRID 483607
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HRID 483607 반응식
[C:1]1([C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][CH:13]=[C:14]([CH:17]=O)[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][C:20]1O[N:23]=[CH:22][CH:21]=1.[Na].Cl.[C:27]([CH2:30][C:31]([O:33][CH2:34][CH2:35][CH3:36])=[O:32])(=[NH:29])[NH2:28].C(O)(=O)C>C(O)CC>[NH2:29][C:27]1[NH:28][C:20]([CH3:19])=[C:21]([C:22]#[N:23])[CH:17]([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:15]=2[CH:16]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[N:9]3)[C:30]=1[C:31]([O:33][CH2:34][CH2:35][CH3:36])=[O:32]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 798335-MethylisoxazoleHCID 5360545SodiumHCID 12391079Propyl amidinoacetate hydrochlorideHCID 151703323-Phenylquinoline-5-carbaldehyde

생성물 1

HCID 67780612n-Propyl 2-amino-1,4-dihydro-5-cyano-6-methyl-4-(3-phenylquinolin-5-yl)-pyridine-3-carboxylate수율 16.3%

시약·촉매·용매 1

HCID 10311-Propanol용매2회

실험 절차

23.3 g (100 mmol) of 3-phenyl-quinoline-5-aldehyde are suspended in 200 ml of n-propanol and the suspension is stirred with 8.25 ml (100 mmol) of 5-methylisoxazole. A solution of 2.3 g of sodium in 100 ml of n-propanol is added dropwise and the mixture is stirred at 40°-50° C. for hours. A brown solution is obtained by this procedure. 8.04 g (100 mmol) of propyl amidinoacetate hydrochloride and 6 ml of acetic acid (100 mmol) are added and the mixture is boiled for 20 hours. It is concentrated, the residue is dissolved in ethyl acetate/water and the phases are separated. The ethyl acetate phase is washed with sodium bicarbonate solution and twice with water, dried and concentrated. The resulting residue is dissolved in 100 ml of hot acetonitrile and the product is left to crystallise. It is filtered off with suction and recrystallised from n-propanol and then from acetonitrile. 6.9 g of colourless crystals of melting point 237° C. are obtained.

후처리

  1. customA brown solution is obtained by this procedure
  2. concentrationIt is concentrated
  3. dissolutionthe residue is dissolved in ethyl acetate/water
  4. customthe phases are separated
  5. washThe ethyl acetate phase is washed with sodium bicarbonate solution and twice with water
  6. customdried
  7. concentrationconcentrated
  8. dissolutionThe resulting residue is dissolved in 100 ml of hot acetonitrile
  9. waitthe product is left
  10. customto crystallise
  11. filtrationIt is filtered off with suction
  12. customrecrystallised from n-propanol

출처 및 근거

ORD 기록
ord-5fa8c79343f24411b7c7cd0b7528d169
출처 데이터셋
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05225558

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