Lithium hydroxide, monohydrate → 3-Bromo-5-[(dimethylamino)methyl]benzoic acid

HRID 1617399ノート

反応式

HRID 1617399 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:11]=1)[C:5]([O:7]C)=[O:6].O.[OH-].[Li+]>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:11]=1)[C:5]([OH:7])=[O:6]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 58187962Methyl 3-bromo-5-((dimethylamino)methyl)benzoate

生成物 1

HCID 584313873-Bromo-5-[(dimethylamino)methyl]benzoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 3-bromo-5-[(dimethylamino)methyl]benzoate (0.30 g, 1.1 mmol, from Step A) was dissolved in tetrahydrofuran (20 mL) and lithium hydroxide monohydrate (0.555 g, 13.2 mmol) in water (6 mL) was added. After stirring for 3 hours, the mixture was rotovapped to remove THF and reduce the volume of water. The mixture was diluted with an equivalent volume of acetonitrile and filtered. The product was purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN/H2O containing 0.15% NH4OH). Solvent was removed from fractions containing desired product by rotary evaporation to afford a white solid. Yield: 0.26 g (91%); LC-MS: 258.0, 260.0 (M+H)+. 1H NMR (300 MHz, DMSO-d6): δ 7.86 (dd, 1H), 7.76 (dd, 1H), 7.43 (dd, 1H), 3.38 (s, 2H), 2.14 (s, 6H).

後処理

  1. customto remove THF
  2. additionThe mixture was diluted with an equivalent volume of acetonitrile
  3. filtrationfiltered
  4. customThe product was purified via preparative HPLC-MS (C18
  5. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)
  6. customSolvent was removed from fractions
  7. additioncontaining desired product
  8. customby rotary evaporation
  9. customto afford a white solid

出典と根拠

ORDレコード
ord-c3d6e8d697464cc888a7884b38cb622b
出典データセット
uspto-grants-2014_07
特許番号
US08765734B2

反応ノート

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