Hydrochloric Acid → Dimethyl 3-aminobenzene-1,2-dicarboxylate

HRID 709534

反応式

HRID 709534 の反応式
Cl.[CH3:2][O:3][C:4](=[O:18])[C:5]1[C:6](=[C:11]([N+:15]([O-])=O)[CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH3:10])=[O:8].[Sn](Cl)Cl>C(O)C>[CH3:2][O:3][C:4](=[O:18])[C:5]1[C:6](=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH3:10])=[O:8]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 2499121,2-Benzenedicarboxylic acid, 3-nitro-, 1,2-dimethyl ester

生成物 1

HCID 13399384Dimethyl 3-aminobenzene-1,2-dicarboxylate収率 86%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 3:1 ethanol-conc. HCl (200 mL) was cooled to 0° C. and then 3-nitrophthalic acid dimethyl ester (15.0 g, 62.8 mmol) was added. Maintaining the cooling, tin (II) chloride (70.8 g, 314 mmol) was added portionwise, over a period of 15 min. Following completion of the addition, the cooling bath was removed and stirring proceeded at room temperature. After 2 h, the mixture was neutralized by the addition of solid sodium bicarbonate, and the resulting mixture was extracted with ethyl acetate (3×150 mL) and the combined extracts were washed with water (5×250 mL), were dried (MgSO4) and evaporated, providing 11.3 g of 3-aminophthalic acid dimethyl ester as a yellow oil, in 86% yield; 1H NMR (CDCl3) δ 3.84 (s, 3H), 3.86 (s, 3H), 5.20 (br, 2H), 6.78 (dd, J=8.5 Hz, J=1.0 Hz, 1H), 6.90 (dd, 1H, J=7.3 Hz, J=1.0 Hz, 1H), 7.24 (t, J=7.8 Hz, 1H).

後処理

  1. additionwas added portionwise, over a period of 15 min
  2. additioncompletion of the addition
  3. customthe cooling bath was removed
  4. customproceeded at room temperature
  5. additionthe mixture was neutralized by the addition of solid sodium bicarbonate
  6. extractionthe resulting mixture was extracted with ethyl acetate (3×150 mL)
  7. washthe combined extracts were washed with water (5×250 mL)
  8. dry with materialwere dried (MgSO4)
  9. customevaporated

出典と根拠

ORDレコード
ord-94ab0c876299494cbde4f6f92ab0dcce
出典データセット
uspto-grants-2015_11
特許番号
US09181216B2

関連ノート

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