Methanesulfonic Acid → HCID 20067461, compound

HRID 443738Notes

Reaction equation

HRID 443738 reaction equation
COC1C=CC(CCN[C:12]([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)O)([CH3:14])C)=CC=1.[NH4+:23].[OH-:24].[CH3:25]S(O)(=O)=O>>[OH:24][C:20]1[CH:19]=[CH:18][C:17]2[CH:15]=[CH:12][CH:14]=[CH:25][NH:23][C:22]=2[CH:21]=1

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 14923Ammonium HydroxideHCID 12570793HCID 12570793, compound

Product 1

HCID 20067461HCID 20067461, compound

Procedure

A stirred solution of 8.0 g (0.0268 mole) of α-(1-{[2-(4-methoxyphenyl)-ethyl]amino}-1-methylethyl)benzenemethanol in 30 ml of methanesulfonic acid is heated for 11 hrs. at 83° C. The brown solution is poured onto ice, made basic with NH4OH and extracted twice with 150 ml of ethyl acetate. The combined organic extracts are washed with saturated aqueous NaCl, dried (Na2SO4) and evaporated in vacuo. Trituration of the residue with hot acetonitrile and cooling gave 1.7 g (27% ) of the above named 8-hydroxybenzazepine derivative as a result of cyclization with simultaneous cleavage of the methoxy function, mp 208°-209° C., dec. An analytical sample melting at 209°-210° C., dec., is obtained by recrystallization from acetonitrile.

Workup

  1. customat 83° C
  2. additionThe brown solution is poured onto ice
  3. extractionextracted twice with 150 ml of ethyl acetate
  4. washThe combined organic extracts are washed with saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. temperatureTrituration of the residue with hot acetonitrile and cooling

Sources & evidence

ORD record
ord-d053d29176404486a10920aecd3dc741
Source dataset
uspto-grants-1981_04
Patent number
US04261890

Reaction notes

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