Hydrochloric Acid → 2-(Quinolin-6-yl)acetic acid

HRID 881045노트

반응식

HRID 881045 반응식
C[O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2.O.[OH-].[Na+].Cl>CO>[N:11]1[C:12]2[C:7](=[CH:6][C:5]([CH2:4][C:3]([OH:15])=[O:2])=[CH:14][CH:13]=2)[CH:8]=[CH:9][CH:10]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 1514202Methyl 6-quinolineacetate

생성물 1

HCID 117887092-(Quinolin-6-yl)acetic acid수율 78.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Sulphuric acid (67.5 ml) was added to 4-Aminophenylacetic acid (45 g, 297 mmol), glycerol (61.7 g, 67 mmol), and iodine (1.14 g, 4 mmol) drop-wise at rt. The mixture was heated to 140° C. for 24 h. After that reaction mixture cooled to rt and pH adjusted to 5 using 10% sodium hydroxide solution. To this methanol (350 ml) and sulphuric acid (3 ml) was added and heated to 100° C. for 24 h. Reaction mixture filtered through celite and filtrate was evaporated on rotavapour to obtain the residue. pH of the residue was adjusted to 5 using 4% NaOH solution and extracted with EtOAc. EtOAc layer was dried on anhydrous Na2SO4 and EtOAc removed on rotavapour to obtain the crude. Crude was purified by column using EtOAc and Petether as eluent to obtain methyl-2-(quinolin-6-yl)acetate (11.2 g). Methyl-2-(quinolin-6-yl)acetate (11.2 g) was dissolved in Methanol (8 ml) and water (8 ml) and added sodium hydroxide (3.3 g, 82 mmol). This mixture stirred for 30 mins and methanol removed on rotavapour to obtain the residue. Residue was acidified to pH 5 using 0.8 N HCl to obtain the solid. Solid was filtered and dried to obtain the title compound (8.2 g).

후처리

  1. custommethanol removed on rotavapour
  2. customto obtain the residue
  3. customto obtain the solid
  4. filtrationSolid was filtered
  5. customdried

출처 및 근거

ORD 기록
ord-4ebbe7fdbdc74f608fe28bd745f33a29
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993612B2

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