Stannous chloride dihydrate → Methyl 3-amino-6-chloro-2-methylbenzoate

HRID 1396619ノート

反応式

HRID 1396619 の反応式
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:12])[C:5]([N+:13]([O-])=O)=[CH:4][CH:3]=1.ClC1C(C(OC)=O)=C(C)C=CC=1[N+]([O-])=O.O.O.Cl[Sn]Cl>CCO>[NH2:13][C:5]1[C:6]([CH3:12])=[C:7]([C:2]([Cl:1])=[CH:3][CH:4]=1)[C:8]([O:10][CH3:11])=[O:9]

参加物

5

反応物 3

HCID 61436Stannous chloride dihydrateHCID 68749648HCID 68749648、化合物HCID 68754758Methyl 6-chloro-2-methyl-3-nitrobenzoate

生成物 1

HCID 21710154Methyl 3-amino-6-chloro-2-methylbenzoate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To above stirred mixture of methyl 6-chloro-2-methyl-3-nitrobenzoate 62 and methyl 6-chloro-2-methyl-5-nitrobenzoate in EtOH (500 mL), SnCl2.2H2O (224 g, 992 mmol, 4 eq) was added and the resulting mixture was stirred at reflux for 3 h. The reaction mixture was allowed to cool to RT and concentrated in vacuo. The residue was poured into water (1 L) and extracted with ethyl acetate (5×500 mL). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (2-10% ethyl acetate-hexanes) to afford the regio-isomer methyl 3-amino-6-chloro-2-methylbenzoate 63.

後処理

  1. additionwas added
  2. stirringthe resulting mixture was stirred
  3. temperatureat reflux for 3 h
  4. concentrationconcentrated in vacuo
  5. additionThe residue was poured into water (1 L)
  6. extractionextracted with ethyl acetate (5×500 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo
  11. customthe residue was purified by flash column chromatography on silica gel (2-10% ethyl acetate-hexanes)

出典と根拠

ORDレコード
ord-122799ea107049a5906d6fad7e1c3743
出典データセット
uspto-grants-2014_12
特許番号
US08901133B2

反応ノート

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