Diethyl Ether → CP-376395

HRID 1637688Notes

Reaction equation

HRID 1637688 reaction equation
CO[C:3](=O)[C:4]1[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1[O:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=1[CH3:26].[Al+3].[Cl-].[Cl-].[Cl-].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)C>C1COCC1>[CH3:3][C:4]1[C:5]([O:17][C:18]2[C:19]([CH3:26])=[CH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[N:6][C:7]([CH3:16])=[CH:8][C:9]=1[NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 232165764-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acid methyl ester

Product 1

HCID 9862166CP-376395Yield 102.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester (prepared as described in Preparation F, 29 mg, 0.078 mmol) and AlCl3 (10 mg,0.078 mmol) in dry THF was added 1 M LiAlH4 in diethyl ether (0.31 ml, 0.31 mmol) at room temperature. After stirring for 10 min, the mixture was heated under reflux for 2 hr. The mixture was quenched with 0.2 ml of water, 0.2 ml of 1N NaOH and 0.4 ml of water and 10 ml of dry THF and stirred for 15 min. The mixture was filtered through Celite® and washed with chloroform. The filtrate was dried over dry sodium sulfate, filtered and concentrated to dryness to give 26 mg (93%) of white solid. 1H NMR (CDC13) δ 6.85(s,2H), 6.08(s,1H), 3.72(d,NH, 1H), 3.35(m,1H), 2.30(s,3H), 2.16(s,3H), 2.13 (s,3H), 2.05(s, 6H), 1.45-1.75(m,4H), 0.98(t,6H) ppm. The corresponding HCl salt was prepared and triturated with diethyl ether to give white solid, mp.212-215° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. customThe mixture was quenched with 0.2 ml of water, 0.2 ml of 1N NaOH and 0.4 ml of water and 10 ml of dry THF
  4. stirringstirred for 15 min
  5. filtrationThe mixture was filtered through Celite®
  6. washwashed with chloroform
  7. dry with materialThe filtrate was dried over dry sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-06e495955b5f4452b9a7c5b75bcf091c
Source dataset
uspto-grants-2000_03
Patent number
US06043260

Reaction notes

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