Aluminium lithium hydride → HCID 21956361, compound

HRID 1640713Notes

Reaction equation

HRID 1640713 reaction equation
[CH3:1][N:2]1[C:10]([CH2:11][O:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:9]2[C:4]([CH:5]=[C:6]([N+:32]([O-])=O)[CH:7]=[CH:8]2)=[N:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][N:2]1[C:10]([CH2:11][O:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:9]2[C:4]([CH:5]=[C:6]([NH2:32])[CH:7]=[CH:8]2)=[N:3]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21956370HCID 21956370, compound

Product 1

HCID 21956361HCID 21956361, compoundYield 127.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methyl-6-nitro-3-[(trityloxy)methyl]-2H-indazole (0.50 g, 1.11 mmol) in anhydrous THF under nitrogen atmosphere at 0° C. was added LiAlH4 (2.7 ml, 1.0 M in THF, 2.7 mmol). The solution was stirred at 0° C. for ˜3 h then cooled to −78° C. and quenched with wet THF. The resulting mixture was conc. in vacuo then repeatedly triturated with CH3CN. The combined CH3CN was conc. in vacuo to give crude 2-methyl-3-[(trityloxy)methyl]-2H-indazol-6-amine (0.593 g, 108% TY). MS (ES+, m/z) 420 (M+H).

Workup

  1. temperaturethen cooled to −78° C.
  2. customquenched with wet THF
  3. customthen repeatedly triturated with CH3CN

Sources & evidence

ORD record
ord-0c8fe2789e3c435094dd6a58f64ff0e5
Source dataset
uspto-grants-2012_02
Patent number
US08114885B2

Reaction notes

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