Hydrochloric Acid → HCID 72579289, compound

HRID 2376619Notes

Reaction equation

HRID 2376619 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[CH2:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[CH:4]=[CH:3]1.[N:14](OCCC(C)C)=[O:15].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl>C1COCC1>[OH:15][N:14]=[C:7]1[C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[CH:4]=[CH:3][N:2]([CH3:1])[C:8]1=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 2733832Lithium HexamethyldisilazideHCID 598557731,3-Dihydro-3-methyl-2H-3-benzazepin-2-one

Product 1

HCID 72579289HCID 72579289, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A THF (0.5 L) solution of 3-methyl-2,3-dihydro-1H-3-benzazepin-2-one (113.8 g, 0.657 mol) was cooled to 0° C. and isoamyl nitrite (100.75 g, 0.86 mol) was added dropwise. To the resulting mixture was added LiHMDS (1 N THF solution, 854 mL, 0.854 mol) at a rate such that the temperature remained below 10° C. After addition, the reaction was allowed to stir at room temperature for 2-3 h while monitoring for the reaction progress by HPLC. Upon completion of the reaction, the mixture was cooled to 0° C., and the pH adjusted from 12 to 2-3 using aqueous HCl (2N). The resulting precipitate was stirred for 12-16 h before isolation by filtration and drying to provide 86.3 g (64.9%) of 1-hydroxyimino-3-methyl-2,3-dihydro-1H-3-benzazepin-2-one; mp=225-226° C.; (M+H)+=203.0.

Workup

  1. customremained below 10° C
  2. additionAfter addition
  3. customUpon completion of the reaction
  4. temperaturethe mixture was cooled to 0° C.
  5. stirringThe resulting precipitate was stirred for 12-16 h before isolation by filtration
  6. customdrying

Sources & evidence

ORD record
ord-ba171a89878e49a1bd1c14e1ebc348cf
Source dataset
uspto-grants-2008_12
Patent number
US07468365B2

Reaction notes

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