HCID 19761446, compound → HCID 19761437, compound

HRID 373833Notes

Reaction equation

HRID 373833 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[NH:23][CH:24]=O>C1COCC1>[CH3:24][NH:23][C:17]1[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=1[C:8]1[NH:7][C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 2

HCID 19761446HCID 19761446, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19761437HCID 19761437, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A total of 123 ml 1M LiAlH4 in THF was added portionwise to a solution of 15.37 g N-[2-(1H-indol-2-yl)-4-chlorophenyl]formamide in 230 ml THF, during which the temperature was maintained below 20° C. The resulting mixture was stirred three hours at room temperature and then quenched with a saturated NH4Cl solution (140 ml). This was then filtered through celite, dried (MgSO4), and concentrated to yield a solid. Purification by HPLC using CH2Cl2 /hexane (2:3) as eluent yielded 7.43 g solid, m.p. 123°-126°.

Workup

  1. temperaturewas maintained below 20° C
  2. customquenched with a saturated NH4Cl solution (140 ml)
  3. filtrationThis was then filtered through celite
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto yield a solid
  7. customPurification by HPLC

Sources & evidence

ORD record
ord-5532cb54cea34ca3874d3f21a812c3e9
Source dataset
uspto-grants-1992_11
Patent number
US05166170

Reaction notes

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