Sodium Hydroxide → 4-({[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}methyl)isophthalic acid

HRID 456849ノート

反応式

HRID 456849 の反応式
[C:1]1([C:7]2[NH:11][C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[CH:18]=[C:17]([O:22][CH2:23][C:24]3[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][C:25]=3[C:34]([O:36]C)=[O:35])[CH:16]=[CH:15]4)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1.CO.O>[C:1]1([C:7]2[NH:11][C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[CH:18]=[C:17]([O:22][CH2:23][C:24]3[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[CH:26][C:25]=3[C:34]([OH:36])=[O:35])[CH:16]=[CH:15]4)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 2

HCID 14798Sodium HydroxideHCID 18439040dimethyl 4-({[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}methyl)isophthalate

生成物 1

HCID 115255174-({[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}methyl)isophthalic acid収率 94%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of dimethyl 4-({[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}methyl)isophthalate (230 mg, 0.468 mmol), prepared in the previous step, and 1 N NaOH (2.81 mL, 2.81 mmol) in 30 mL of THF plus 20 mL of methanol plus 5 mL of water was refluxed under nitrogen for 7 h. The reaction was filtered, cooled to room temperature, acidified by the addition of 5 mL of 1 N HCl and then concentrated under reduced pressure to remove the THF and methanol. The solid present was collected by filtration, rinsed with water and dried under reduced pressure at 60° C. to give the title compound (204 mg, 94%) as a yellow solid, mp 289–291° C. Elemental Analysis for C29H21NO5.0.40 C4H8O.0.22 H2O Calc'd: C, 74.06; H, 5.00; N, 2.82. Found: C, 73.83; H, 5.19; N, 2.70.

後処理

  1. temperaturewas refluxed under nitrogen for 7 h
  2. filtrationThe reaction was filtered
  3. additionacidified by the addition of 5 mL of 1 N HCl
  4. concentrationconcentrated under reduced pressure
  5. customto remove the THF and methanol
  6. filtrationThe solid present was collected by filtration
  7. washrinsed with water
  8. customdried under reduced pressure at 60° C.

出典と根拠

ORDレコード
ord-6fd1259feb094bb49e164f92e5d4e9ac
出典データセット
uspto-grants-2007_03
特許番号
US07186749B2

反応ノート

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