Water → HCID 13067118, compound

HRID 2296317Notes

Reaction equation

HRID 2296317 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]1[CH:14]=[C:13]2[C:7]([CH2:8][N:9]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:11]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:12]=32)=[CH:6]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[Cl:19][C:17]1[CH:16]=[CH:15][C:12]2[C:13]3[C:7](=[CH:6][N:5]([CH2:4][CH2:3][OH:2])[CH:14]=3)[CH2:8][N:9]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:11]=2[CH:18]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13067116HCID 13067116, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 13067118HCID 13067118, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.3 g (6.0 mmol) of 8-chloro-6-(2-fluorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-acetic acid methyl ester in 25 ml of tetrahydrofuran was added dropwise to a solution of 0.5 g (13 mmol) of lithium aluminum hydride in 30 ml of tetrahydrofuran which was cooled to -78°. The reaction was allowed to warm to 0° and was stirred for 2 hr. The excess lithium aluminum hydride was discharged by the addition of 0.6 ml of water, 0.6 ml of 10% sodium hydroxide and 2.0 ml of water. The resulting precipitate was removed by filtration and the filtrate was concentrated at reduced pressure to dryness. The residue crystallized from ether to give a white solid. Recrystallization from a mixture of ether and petroleum ether gave colorless prisms, mp 145°-147°.

Workup

  1. temperaturewas cooled to -78°
  2. temperatureto warm to 0°
  3. customThe resulting precipitate was removed by filtration
  4. concentrationthe filtrate was concentrated at reduced pressure to dryness
  5. customThe residue crystallized from ether
  6. customto give a white solid
  7. customRecrystallization
  8. additionfrom a mixture of ether and petroleum ether
  9. customgave colorless prisms, mp 145°-147°

Sources & evidence

ORD record
ord-cec12ddc6af44ff8b6b7f0550776c6d0
Source dataset
uspto-grants-1984_01
Patent number
US04428879

Reaction notes

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