Hydrochloric Acid → HCID 136332178, compound

HRID 235603Notes

Reaction equation

HRID 235603 reaction equation
C(C1C(=O)[CH2:8][CH:9]([C:13]2[C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:16]([CH3:23])=[N:15][C:14]=2[Cl:24])[CH2:10][C:11]=1O)(=O)CCC.Cl.[CH2:27]([O:29][NH2:30])[CH3:28].[OH-:31].[Na+].Cl.[CH2:34]([OH:36])[CH3:35]>>[Cl:24][C:14]1[N:15]=[C:16]([CH3:23])[C:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=2[C:13]=1[CH:9]1[CH2:10][CH2:11][C:34](=[O:36])[C:35]([C:8](=[N:30][O:29][CH2:27][CH3:28])[CH2:9][CH2:10][CH3:11])=[C:8]1[OH:31]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 178450336HCID 178450336, compound

Product 1

HCID 136332178HCID 136332178, compound

Procedure

A mixture of 2-butyryl-5-(3-chloro-1-methyl-5,6,7,8-tetrahydroisoquinolin-4-yl)-3-hydroxycyclohex-2-en-1-one (2.07 g), ethoxyamine hydrochloride (1.1 equiv), sodium hydroxide (1.1 equiv in 0.5 ml water) and ethanol (40 ml) was stirred at room temperature for 3 hr. The mixture was poured into a very dilute hydrochloric acid solution, which was then immediately extracted with diethyl ether. The dried (MgSO4) organic extract was evaporated to give 5-(3-chloro-1-methyl-5,6,7,8-tetrahydroisoquinolin-4-yl-2-[1-(ethoxyimino)butyl]-3-hydroxycyclohex-2-en-1-one as a white solid, mp 141° C. The product was characterized by proton nuclear magnetic resonance spectroscopy and the spectroscopic data is recorded in Table 4, Example 10.

Workup

  1. extractionwas then immediately extracted with diethyl ether
  2. dry with materialThe dried (MgSO4)
  3. extractionorganic extract
  4. customwas evaporated

Sources & evidence

ORD record
ord-cdbadb011f7943a996262ccdd1234aa3
Source dataset
uspto-grants-1987_02
Patent number
US04640708

Reaction notes

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