Water → HCID 12340644, compound

HRID 259037Notes

Reaction equation

HRID 259037 reaction equation
[CH3:1][N:2]([CH3:20])[C:3](=O)[CH2:4][C:5]1([CH3:18])[C:10]2=[CH:11][CH:12]=[CH:13][N:9]2[C:8]2[CH:14]=[CH:15][CH:16]=[CH:17][C:7]=2[O:6]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[CH3:20][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1([CH3:18])[C:10]2=[CH:11][CH:12]=[CH:13][N:9]2[C:8]2[CH:14]=[CH:15][CH:16]=[CH:17][C:7]=2[O:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 12340639HCID 12340639, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12340644HCID 12340644, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of the amide of formula 3, N,N,4-trimethyl-4H-pyrrolo-[2,1-c][1,4]benzoxazin-4-acetamide (5 g), described in Example 14, in 150 ml of ether is added dropwise to a suspension of lithium aluminum hydride (2.6 g) in anhydrous ether (350 ml). The reaction mixture is stirred at room temperature for 4 hr. Decomposition of the mixture with 11 ml of water gives a white precipitate, which is collected on a filter and washed with ether. The filtrate is extracted with 2% aqueous HCl. The extract is rendered basic with a 10% solution of NaOH and extracted with chloroform. The chloroform extract is dried (MgSO4), filtered and evaporated to give the title compound, nmr (CDCl3) δ 1.61 (s, b 3H), 2.18 (s, 6H), 2.25 (m, 4H), 5.98 (m, 1H), 6.30 (6, J = 3.5 Hz, 1H), 6.9 - 7.5 (m, 5H).

Workup

  1. customis collected on
  2. filtrationa filter
  3. washwashed with ether
  4. extractionThe filtrate is extracted with 2% aqueous HCl
  5. extractionextracted with chloroform
  6. extractionThe chloroform extract
  7. dry with materialis dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-74ce2e1406de4faa91ed843f8a9c4d27
Source dataset
uspto-grants-1977_07
Patent number
US04035495

Reaction notes

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