Water → 6-(3-Hydroxypropyl)-2-methyl-5,6-dihydropyrrolo[1,2-c]quinazoline

HRID 65928Notes

Reaction equation

HRID 65928 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[CH:9]=[C:10]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]([CH2:20][CH2:21][C:22](OC)=[O:23])[C:12](=O)[N:11]2[CH:27]=1.O.[OH-].[Na+]>CCOCC>[OH:23][CH2:22][CH2:21][CH2:20][N:13]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[C:10]2=[CH:9][C:8]([CH3:7])=[CH:27][N:11]2[CH2:12]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 227563572-Methyl-6-(beta-carbomethoxyethyl)pyrrolo[1,2-c]quinazolin-5-one

Product 1

HCID 227563636-(3-Hydroxypropyl)-2-methyl-5,6-dihydropyrrolo[1,2-c]quinazoline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

LiAlH4 (2.88 g, 0.076 m) was slurried in ether (250 ml) and to this was added a solution of the product of Example XXXV (5.5 g, 0.019 m) in ether (100 ml). The reaction mixture was stirred at ambient temperature for 1/2 hr. To the reaction mixture was added dropwise and successively H2O (3.0 ml), NaOH (3.0 ml of 15% aqueous), and H2O (9.0 ml). The resulting precipitate was filtered and washed with ether. The solvent was removed in vacuo from the filtrate and the residue crystallized from pentane to yield the desired product as a pale yellow solid; m.p. 77°-78° C.

Workup

  1. additionTo the reaction mixture was added dropwise
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with ether
  4. customThe solvent was removed in vacuo from the filtrate
  5. customthe residue crystallized from pentane

Sources & evidence

ORD record
ord-b6102c0ae1624cf5b385ea293eb4eb34
Source dataset
uspto-grants-1978_12
Patent number
US04129653

Reaction notes

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