Ammonia → HCID 21404768, compound

HRID 972519Notes

Reaction equation

HRID 972519 reaction equation
O[CH:2]1[C:11]2[CH:10]=[N:9][C:8]([O:12][CH3:13])=[CH:7][C:6]=2[CH2:5][CH2:4][CH:3]1[CH2:14][C:15]([O-:17])=[O:16].S(=O)(=O)(O)O.N>>[CH3:13][O:12][C:8]1[N:9]=[CH:10][C:11]2[CH2:2][CH:3]([CH2:14][C:15]([OH:17])=[O:16])[CH:4]=[CH:5][C:6]=2[CH:7]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 21404790HCID 21404790, compound

Product 1

HCID 21404768HCID 21404768, compound

Procedure

11 Parts of 8-hydroxy-3-methoxy-5,6,7,8-tetrahydro-2-azanaphthalene-7-acetate described in Example 25 is added to 110 parts by volume of sulfuric acid at room temperature and stirred for 15 minutes. 200 Parts of ice water are added and the solution is made basic with 300 parts by volume of aqueous ammonia. The solution is filtered through celite and then extracted three times with chloroform. Removal of the chloroform and crystallization from methanol provides 3-methoxy-7,8-dihydro-2-azanaphthalene-7-acetic acid, melting at 151°-152° C. This compound is also an active anti-inflammatory agent, as is the alkylated derivative, 3-methoxy-7,8-dihydro-2-azanaphthalene-7-α-methylacetic acid.

Workup

  1. filtrationThe solution is filtered through celite
  2. extractionextracted three times with chloroform
  3. customRemoval of the chloroform and crystallization from methanol

Sources & evidence

ORD record
ord-c18dbd8e3d2e46c1b70fc9424e153469
Source dataset
uspto-grants-1977_10
Patent number
US04053476

Reaction notes

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