Sodium Hydroxide → HCID 178507813, compound

HRID 129026Notes

Reaction equation

HRID 129026 reaction equation
[N:1]([C:4]1[C:5](=[O:28])[C:6]2[C:11]([C:12](=[O:27])[C:13]=1[C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[CH2:16][CH2:15]1)=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.O>[NH2:1][C:4]1[C:5](=[O:28])[C:6]2[C:11]([C:12](=[O:27])[C:13]=1[C@H:14]1[CH2:15][CH2:16][C@H:17]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[CH2:18][CH2:19]1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178514503HCID 178514503, compound

Product 1

HCID 178507813HCID 178507813, compoundYield 23.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

The impure product of stage (a) (0.9 g) was dissolved in dry tetrahydrofuran (THF) and added dropwise to a suspension of lithium aluminium hydride (2.0 g) in THF. The mixture was stirred at room temperature for 1 hour and then 2.0 ml of water was added dropwise with caution. A current of air was passed through the mixture for 1 hour and then 0.7 g of sodium hydroxide in 6 ml of water was added. The mixture was filtered and washed with THF. The filtrate was evaporated to dryness leaving an amorphous orange material which was triturated with SVM whereupon orange crystals formed. These were filtered off, washed well with SVM and dried to yield a first crop of product (200 mg) mp210°-215°. The reaction was repeated to give a further crop of product (300 mg) mp200°-210°. The two crops were combined and chromatographed, eluting with chloroform, to give the title compound (350 mg) mp212°-215°.

Workup

  1. waitA current of air was passed through the mixture for 1 hour
  2. filtrationThe mixture was filtered
  3. washwashed with THF
  4. customThe filtrate was evaporated to dryness
  5. customleaving an amorphous orange material which
  6. customwas triturated with SVM whereupon orange crystals
  7. customformed
  8. filtrationThese were filtered off
  9. washwashed well with SVM
  10. customdried

Sources & evidence

ORD record
ord-63919d7c21544ce4936557b975a9042e
Source dataset
uspto-grants-1995_11
Patent number
US05466711

Reaction notes

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