Sodium borohydride → HCID 178469470, compound

HRID 1194551Notes

Reaction equation

HRID 1194551 reaction equation
[OH:1][C:2]1[C:11]2[CH2:10][C:9](=[O:12])[CH2:8][CH2:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[BH4-].[Na+]>C(O)C>[CH2:16]([O:15][C:13]([C:3]1[CH:4]=[N:5][C:6]2[CH2:7][CH2:8][CH:9]([OH:12])[CH2:10][C:11]=2[C:2]=1[OH:1])=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178469469HCID 178469469, compound

Product 1

HCID 178469470HCID 178469470, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 6 g of ethyl 4-hydroxy-6-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate in 200 mL of ethanol, 1.92 g of NaBH4 is added in small portions under ice-cooling and stirring. The reaction mixture is then stirred at room temperature for 6 hours and evaporated to dryness. The residue is taken up in CHCl3, washed successively with 6N NH4OH, and sat. aq. NaCl, dried (MgSO4) and evaporated dryness obtaining ethyl-4,6-dihydroxy-5,6,7,8-tetrahydroquinoline-3-carboxylate.

Workup

  1. additionis added in small portions under ice-
  2. temperaturecooling
  3. stirringThe reaction mixture is then stirred at room temperature for 6 hours
  4. customevaporated to dryness
  5. washwashed successively with 6N NH4OH, and sat. aq. NaCl
  6. dry with materialdried (MgSO4)
  7. customevaporated dryness

Sources & evidence

ORD record
ord-26637c872253497e97a120c3bee2dc93
Source dataset
uspto-grants-1989_03
Patent number
US04814450

Reaction notes

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