Hydrochloric Acid → HCID 59377940, 화합물

HRID 2065737노트

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HRID 2065737 반응식
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([CH3:11])=[CH:6][C:5]=1[Cl:12].[BH4-].[Li+].Cl.[OH-].[Na+]>C1COCC1>[NH2:10][C:8]1[C:7]([CH3:11])=[CH:6][C:5]([Cl:12])=[C:4]([CH2:3][OH:2])[CH:9]=1

참가 물질

6

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HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 57423009Benzoic acid, 5-amino-2-chloro-4-methyl-, methyl ester

생성물 1

HCID 59377940HCID 59377940, 화합물수율 73.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 5-amino-2-chloro-4-methyl-benzoic acid methyl ester (0.44 g, 2.204 mmol) in THF (5 ml) was added lithium borohydride (012 g, 5.509 mmol). The mixture was heated at reflux for three hours. The mixture was cooled to 0° C., acidified with 2N aqueous HCl, and the mixture was stirred for 10 minutes. The mixture was taken to pH7 with 2N aqueous NaOH and the product was extracted with EtOAc. The combined extracts were washed with water, brine dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 6:4) gave 0.278 g (73%) of (5-amino-2-chloro-4-methyl-phenyl)-methanol as a white solid.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for three hours
  3. extractionthe product was extracted with EtOAc
  4. washThe combined extracts were washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification of the crude product by flash chromatography (hexanes:EtOAc 6:4)

출처 및 근거

ORD 기록
ord-01819287292244a89cbb3dee5cda17f6
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288552B2

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