Hydrochloric Acid → HCID 13243539, compound

HRID 2418753Notes

Reaction equation

HRID 2418753 reaction equation
[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:7]=2[N:6]([CH2:17][C:18]([OH:20])=[O:19])[C:5]1=[O:21])=[N+]=[N-].Cl>C(O)C.O.[Pd]>[NH2:1][CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:7]=2[N:6]([CH2:17][C:18]([OH:20])=[O:19])[C:5]1=[O:21]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 13243507HCID 13243507, compound

Product 1

HCID 13243539HCID 13243539, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-azido-1-carboxymethyl-8-methoxy-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one (11 g) in a mixture of ethanol (250 ml) and water (50 ml) was hydrogenated for 3 hours on a Parr shaker at 3 atmospheres pressure and room temperature using 10% Pd-C (0.5 g) as catalyst. 2N Hydrochloric acid (50 ml) was added, and the catalyst was filtered off. The solvent was removed at reduced pressure, and the residue dissolved in a mixture of water (50 ml) and ethanol (50 ml). Propylene oxide (25 ml) was added and the mixture was stirred for 1 hour. The solvents were removed under reduced pressure to give 3-amino-1-carboxymethyl-8-methoxy-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one, m.p. >300°.

Workup

  1. filtrationthe catalyst was filtered off
  2. customThe solvent was removed at reduced pressure
  3. dissolutionthe residue dissolved in a mixture of water (50 ml) and ethanol (50 ml)
  4. additionPropylene oxide (25 ml) was added
  5. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-50d7aad9a5954df4982895537164258c
Source dataset
uspto-grants-1984_09
Patent number
US04473575

Reaction notes

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