Hydrochloric Acid → HCID 59377940、化合物

HRID 2065737ノート

反応式

HRID 2065737 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 59377940HCID 59377940、化合物収率 73.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-01819287292244a89cbb3dee5cda17f6
出典データセット
uspto-grants-2012_10
特許番号
US08288552B2

反応ノート

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