Water → HCID 13911912, compound

HRID 544456Notes

Reaction equation

HRID 544456 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[C:16]2[N:17]([C:21]([CH3:28])=[C:22]([C:24](OC)=[O:25])[N:23]=2)[CH:18]=[CH:19][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>O1CCCC1>[CH2:7]([O:14][C:15]1[C:16]2[N:17]([C:21]([CH3:28])=[C:22]([CH2:24][OH:25])[N:23]=2)[CH:18]=[CH:19][CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13911911HCID 13911911, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13911912HCID 13911912, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
3 °C

Procedure

To an ice-cooled suspension of LiAlH4 (1.03 g) in tetrahydrofuran (THF) (200 ml) there was added 8-benzyloxy-2-methoxycarbonyl-3-methyl-imidazo[1,2-a]pyridine (13.3 g) obtained according to Example VI in several portions over 20 minutes. The temperature was maintained below +8° C. After all the substance hadbeen added, stirring with cooling was continued for 30 min. and thereafter the mixture was stirred at room temperature for another hour. The reactionmixture was cooled to 3° C. and to the stirred mixture there was first added 1.09 ml of water, then 1.63 ml of 10% aqueous NaOH and finally3.27 ml water. The resulting mixture was stirred for 5 min. on the ice bathand 5 min. at room temperature and then filtered. The solid was washed with2×100 ml of hot THF and the wash fluid was added to the original filtrate. The solution was stripped to yield a brown powder which was triturated for 1 hr. in 150 ml CHCl3. After filtration and washing a slightly impure product was obtained (m.p. 172°- 175° C.).

Workup

  1. customobtained
  2. temperatureThe temperature was maintained below +8° C
  3. additionAfter all the substance hadbeen added
  4. temperaturewith cooling
  5. waitwas continued for 30 min.
  6. stirringthe mixture was stirred at room temperature for another hour
  7. filtrationfiltered
  8. washThe solid was washed with2×100 ml of hot THF
  9. additionthe wash fluid was added to the original filtrate
  10. customto yield a brown powder which
  11. customwas triturated for 1 hr
  12. filtrationAfter filtration
  13. washwashing a slightly impure product
  14. customwas obtained (m.p. 172°- 175° C.)

Sources & evidence

ORD record
ord-2bb4fd1b9205483aa6b1ec24c2fa5097
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

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