Water → HCID 11131622, compound

HRID 746094Notes

Reaction equation

HRID 746094 reaction equation
[C:1]([C:5]1[N:6]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:8][N:9]=1)(OC)=[O:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[OH:2][CH2:1][C:5]1[N:6]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]=[CH:8][N:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13655992HCID 13655992, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11131622HCID 11131622, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of XXIX (1.1 g, 0.003 mol) in dry THF (10 mL) was added dropwise with stirring at 0°-4° C. to a suspension of LAH (0.14 g, 0.0036 mol) in dry THF (10 mL). The mixture was stirred at room temperature, further cooled, H2O (0.13 mL) added, followed by 10% NaOH (0.2 mL) and finally H2O (0.33 mL). The mixture was stirred at room temperature for 30 minutes, then at 0° C. for 1 hour, filtered and the collected solid, washed with THF, hot EtOH (2x) and CHCl3. The combined filtrates were concentrated to dryness. The residue was triturated with hot absolute EtOH to yield 0.7 g (69%) of XXX; m.p. 243°-4°.

Workup

  1. temperaturefurther cooled
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. filtrationfiltered
  4. washthe collected solid, washed with THF, hot EtOH (2x) and CHCl3
  5. concentrationThe combined filtrates were concentrated to dryness
  6. customThe residue was triturated with hot absolute EtOH

Sources & evidence

ORD record
ord-90b5e7012d8c4cda9f32a7fbe7a0c603
Source dataset
uspto-grants-1986_07
Patent number
US04602093

Reaction notes

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