Hydrochloric Acid → HCID 20238659, compound

HRID 364963Notes

Reaction equation

HRID 364963 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[C:6]([CH:10]3[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([C:21]([F:24])([F:23])[F:22])[NH:13][C:12]([CH:25]=[O:26])=[C:11]3[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:7][CH:8]=[CH:9][C:2]=12.[BH4-].[Na+].Cl>C(O)C>[N:1]1[O:5][N:4]=[C:3]2[C:6]([CH:10]3[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([C:21]([F:24])([F:23])[F:22])[NH:13][C:12]([CH2:25][OH:26])=[C:11]3[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20238646HCID 20238646, compound

Product 1

HCID 20238659HCID 20238659, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of diethyl 4-(4-benzofurazanyl)-2-formyl-1,4-dihydro-6-(trifluoromethyl)-3,5-pyridinedicarboxylate (1.1 g; 2.5 mmoles) in dry ethanol (90 ml) was cooled to 0° and sodium borohydride (0.14 g; 3.7 mmoles) was added portionwise over 3 minutes. After 10 minutes, 10% aqueous hydrochloric acid was added dropwise to pH3, and the mixture concentrated in vacuo at room temperature. The resulting yellow oil was dissolved in ether (50 ml) and saturated aqueous sodium bicarbonate was added to pH9. The organic solution was separated, washed with saturated aqueous sodium bicarbonate solution, water, brine and dried (MgSO4). Evaporation of the solvent left a yellow oil which was crystallised from 2-propanol to give the title compound (0.5 g) mp 110°-11°.

Workup

  1. concentrationthe mixture concentrated in vacuo at room temperature
  2. dissolutionThe resulting yellow oil was dissolved in ether (50 ml)
  3. additionsaturated aqueous sodium bicarbonate was added to pH9
  4. customThe organic solution was separated
  5. washwashed with saturated aqueous sodium bicarbonate solution, water, brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent
  8. waitleft a yellow oil which
  9. customwas crystallised from 2-propanol

Sources & evidence

ORD record
ord-80b98bfd7c764c878492cc274fcd88fa
Source dataset
uspto-grants-1986_08
Patent number
US04607041

Reaction notes

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