Ammonium Hydroxide → HCID 20394933, compound

HRID 261444Notes

Reaction equation

HRID 261444 reaction equation
[ClH:1].[C:2]([C:9]1[C:19]2[CH2:18][CH2:17][NH:16][CH2:15][CH:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:13]=2[CH:12]=[C:11]([O:26]C)[C:10]=1[O:28]C)([O:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:3].[OH-].[NH4+].O=C1O[C@H]([C@H](CO)O)C(O)=C1O.C(=O)([O-])[O-]>C(Cl)Cl.B(Br)(Br)Br>[ClH:1].[C:2]([C:9]1[C:19]2[CH2:18][CH2:17][NH:16][CH2:15][CH:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:13]=2[CH:12]=[C:11]([OH:26])[C:10]=1[OH:28])([O:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:3]

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 19660Carbonate IonHCID 20394978HCID 20394978, compoundHCID 54670067L-Ascorbic Acid

Product 1

HCID 20394933HCID 20394933, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25134Boron tribromideSolvent

Procedure

The product from Examples 3 (5.7 g, 0.0136 mole) was dissolved in 500 ml of methylene chloride with 5.1 ml of boron tribromide at -15°. After 4 hours, 25 ml of conc. ammonium hydroxide was added with a small amount of ascorbic acid. The pH was taken to 8 with carbonate solution. The water layer was separated and extracted with ethyl acetate using sodium chloride to salt out the product which was collected and stirred with dilute hydrochloric acid overnight. The mixture was filtered. The filtrate was stripped until a solid formed. Cooling gave the desired 6-carbobutoxy-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride, m.p. 217°-220° (dec.).

Workup

  1. customThe water layer was separated
  2. extractionextracted with ethyl acetate
  3. customwas collected
  4. filtrationThe mixture was filtered
  5. customformed
  6. temperatureCooling

Sources & evidence

ORD record
ord-84276e8452984123bcf47770fb13c4c0
Source dataset
uspto-grants-1979_08
Patent number
US04165372

Reaction notes

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