Water → 4-[(Dimethylamino)methyl]-4-methyl-4H-pyrrolo[2,1-c][1,4]-benzoxazine

HRID 259038Notes

Reaction equation

HRID 259038 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]([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)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[CH3:19][N:2]([CH2:3][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)[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 12340637N,N,4-Trimethyl-4H-pyrrolo[2,1-c][1,4]benzoxazine-4-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 123406424-[(Dimethylamino)methyl]-4-methyl-4H-pyrrolo[2,1-c][1,4]-benzoxazine

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]benzoxazine-4-carboxamide (3 g), described in Example 15 in 50 ml of ether is added dropwise to a suspension of lithium aluminum hydride (1.5 g) in anhydrous ether (100 ml) over a period of 30 min. The reaction mixture is stirred at room temperature for 16 hr. Decomposition of the mixture with 6 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 (DMSO-d6) δ 1.85 (s, 3H), 2.78 (s, 6H).

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-06cbda73d51744e388e380869a3b6119
Source dataset
uspto-grants-1977_07
Patent number
US04035495

Reaction notes

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