Aluminium lithium hydride → HCID 86629451, compound

HRID 599294Notes

Reaction equation

HRID 599294 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([NH:11][C:12]1[C:17]([C:18](OCC)=[O:19])=[CH:16][N:15]=[C:14]([Cl:23])[CH:13]=1)([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([NH:11][C:12]1[CH:13]=[C:14]([Cl:23])[N:15]=[CH:16][C:17]=1[CH2:18][OH:19])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86629450HCID 86629450, compound

Product 1

HCID 86629451HCID 86629451, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 ((2.1 g, 54.7 mmol) was added portion wise to a 0° C. solution of ethyl 4-(tert-butylamino)-6-chloronicotinate (7 g, 27.3 mmol) in THF (100 mL). After 20 min, the reaction was quenched by the addition of water (2.1 mL), followed by 2 N aq NaOH (2 N, 2.1 ml. The resulting suspension was filtered and the filtrate was concentrated to afford (4-tert-butylamino-6-chloro-pyridin-3-yl)-methanol (5.0 g, 86.2% yield), which was used in next step without purification. 1H NMR (400 MHz, DMSO-d6): δ 7.73 (s, 1 H), 6.61 (s, 1 H), 5.87 (s, 1 H), 5.43 (t, J=5.2 Hz, 1 H), 4.38 (d, J=5.2 Hz, 2 H), 1.35 (s, 9 H).

Workup

  1. customthe reaction was quenched by the addition of water (2.1 mL)
  2. filtrationThe resulting suspension was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7fc72e21190b4db19c95ef97ee2b877c
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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