1,2-Benzenedicarboxylic acid, 4-nitro-, 1,2-dimethyl ester → Dimethyl 4-aminophthalate

HRID 63395

反応式

HRID 63395 の反応式
[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:5](=[CH:10][C:11]([N+:14]([O-])=O)=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:5](=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

参加物

4

反応物 1

HCID 691191,2-Benzenedicarboxylic acid, 4-nitro-, 1,2-dimethyl ester

生成物 1

HCID 95886Dimethyl 4-aminophthalate収率 97.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of dimethyl-4-nitrophthalate (15.0 g, 62.7 mmol) and 10% Pd—C (1.5 g) in ethyl acetate (100 mL) was hydrogenated at 50 psi overnight. The reaction mixture was filtered through Celite, and the filter was washed with additional ethyl acetate (50 mL). The solvent was evaporated, and the residue was stirred in hexanes. The solid was filtered, washed with additional hexanes and dried to give 12.77 g of 4-amino-phthalic acid dimethyl ester as a pale orange solid, in 97% yield; 1H NMR (DMSO-d6) δ 3.71 (s, 3H), 3.75 (s, 3H), 6.17 (s, 2H), 6.58-6.65 (m, 2H), 7.57 (d, J=8.4 Hz, 1H).

後処理

  1. customwas hydrogenated at 50 psi overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. washthe filter was washed with additional ethyl acetate (50 mL)
  4. customThe solvent was evaporated
  5. filtrationThe solid was filtered
  6. washwashed with additional hexanes
  7. customdried

出典と根拠

ORDレコード
ord-f91662bc3a684465980f2361b85df7c4
出典データセット
uspto-grants-2016_09
特許番号
US09447070B2

関連ノート

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