Ammonia → HCID 20359294, compound

HRID 2083173Notes

Reaction equation

HRID 2083173 reaction equation
[OH-].[NH4+].O.[CH3:4][N:5]([CH3:25])[CH2:6][CH2:7][C:8]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10](=[O:11])[O:9]1.N>[Zn].C(O)C>[CH3:25][N:5]([CH3:4])[CH2:6][CH2:7][CH:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:18][C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:10]([OH:11])=[O:9]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 14923Ammonium HydroxideHCID 101085553-(2-Dimethylaminoethyl)-3,4-dihydro-3-phenylisocoumarin

Product 1

HCID 20359294HCID 20359294, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

To a well stirred suspension of 45 g. of zinc dust, 90 ml. of concentrated ammonium hydroxide, 45 ml. of water and 2 ml. of cupric sulfate maintained at 80° C. there is added 14.75 g. (0.05 mole) of 3-(2-dimethylaminoethyl)-3,4-dihydro-3-phenylisocoumarin in 50 ml. ethanol for about 30 minutes. The resulting mixture is heated at 85° C. for 30 hours while a slow stream of ammonia is passed through. The mixture is filtered while under heat and the solids washed throughly with 100 ml. of hot ammonium hydroxide. The combined filtrates are cooled and carefully acidified with concentrated hydrochloric acid to give 2-(β-[-2-dimethylaminoethyl]phenethyl)benzoic acid, m.p. 152° to 154° C.

Workup

  1. additionsuspension of 45 g
  2. additionthere is added 14.75 g
  3. filtrationThe mixture is filtered while
  4. temperatureunder heat
  5. washthe solids washed throughly with 100 ml
  6. temperatureThe combined filtrates are cooled

Sources & evidence

ORD record
ord-ef6b8b68f41b43c7bfc76cb2c5eba972
Source dataset
uspto-grants-1978_04
Patent number
US04083997

Reaction notes

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