Aluminium lithium hydride → HCID 44248849, compound

HRID 1443898Notes

Reaction equation

HRID 1443898 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11]3=[C:12]([C:14]4[CH2:20][CH2:19][CH2:18][CH2:17][C:16](=O)[C:15]=4[N:10]3[CH2:9][CH2:8][CH2:7]2)[CH:13]=1)([O-])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCOCC1>[CH:13]1[C:12]2[C:14]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[N:10]3[C:11]=2[C:6]([CH2:7][CH2:8][CH2:9]3)=[CH:5][C:4]=1[NH2:1]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59168383HCID 59168383, compound

Product 1

HCID 44248849HCID 44248849, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 2-nitro-8-oxo-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinoline (0.17 g, 0.60 mmol; prepared in Example 23, Step 1) in dioxane (5 mL) is added dropwise to a refluxing slurry of LiAlH4 (0.24 g, 6 mmol) in dioxane (20 mL). The reaction mixture was refluxed overnight. After cooling to ambient temperature, the mixture was poured onto ice water and extracted with ethyl acetate. The combined organic extracts were dried over MgSO4 and concentrated to give 0.11 g of 5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-amine.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. additionthe mixture was poured onto ice water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c253237dd64d45a693021511840f2ec9
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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