Sodium Bicarbonate → HCID 21314005, compound

HRID 971436Notes

Reaction equation

HRID 971436 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]([NH:13][CH2:14][CH:15]([C:17]2[CH:18]=[CH:19][C:20]([OH:27])=[C:21]([CH:26]=2)[C:22]([O:24]C)=O)O)[CH3:12])=[CH:5][CH:4]=1.C(=O)(O)[O-:29].[Na+]>>[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH:11]([NH:13][CH2:14][C:15]2[C:21]([CH2:22][OH:24])=[C:20]([OH:27])[CH:19]=[CH:18][C:17]=2[CH2:26][OH:29])[CH3:12])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 12814702HCID 12814702, compound

Product 1

HCID 21314005HCID 21314005, compound

Procedure

5-[2-[[3-(4-Fluorophenyl)-1-methylpropyl]amino]-1-hydroxyethyl]-2-hydroxybenzoic acid, methyl ester, hydrochloride (2.66 g) was basified with 8% sodium bicarbonate solution (100 ml) and the free base was extracted into ether (3×100 ml). The dry extracts (MgSO4) were evaporated and the residual oil in tetrahydrofuran (40 ml) was added dropwise under nitrogen to a stirred solution of lithium aluminium hydride (0.74 g) in tetrahydrofuran (40 ml). When the addition was complete, the mixture was stirred at room temperature for 16 hours. The excess hydride was decomposed by the cautious addition of water (10 ml) and then the mixture was evaporated to dryness. The residue was diluted with 2 N hydrochloric acid (100 ml), basified with solid sodium bicarbonate and extracted with ether (2×50 ml). The combined extracts were dried (MgSO4) and diluted with light petroleum (b.p. 60°-80°) until turbid. The product precipitated as an off-white crystalline solid (1.21 g), m.p. 101°-103°. Recrystallization from ether-light petroleum (b.p. 60°-80°) gave colourless needles, m.p. 102°-103°.

Workup

  1. extractionthe free base was extracted into ether (3×100 ml)
  2. customThe dry extracts (MgSO4) were evaporated
  3. additionthe residual oil in tetrahydrofuran (40 ml) was added dropwise under nitrogen to a stirred solution of lithium aluminium hydride (0.74 g) in tetrahydrofuran (40 ml)
  4. additionWhen the addition
  5. additionThe excess hydride was decomposed by the cautious addition of water (10 ml)
  6. customthe mixture was evaporated to dryness
  7. additionThe residue was diluted with 2 N hydrochloric acid (100 ml)
  8. extractionextracted with ether (2×50 ml)
  9. dry with materialThe combined extracts were dried (MgSO4)
  10. additiondiluted with light petroleum (b.p. 60°-80°) until turbid
  11. customThe product precipitated as an off-white crystalline solid (1.21 g), m.p. 101°-103°
  12. customRecrystallization from ether-light petroleum (b.p. 60°-80°)
  13. customgave colourless needles, m.p. 102°-103°

Sources & evidence

ORD record
ord-ad6a64c27a7a4128a7f93a82bd37eb23
Source dataset
uspto-grants-1979_07
Patent number
US04160036

Reaction notes

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