Hydrochloric Acid → 4-[3-(alpha-Naphthyloxy)propyl]aminobenzoic acid

HRID 443645Notes

Reaction equation

HRID 443645 reaction equation
[C:1]1([O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[K+].C(O)C.Cl>O>[C:1]1([O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 23468296Ethyl 4-[3-(1-naphthyloxy)propylamino]benzoate

Product 1

HCID 234682834-[3-(alpha-Naphthyloxy)propyl]aminobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6 g. of ethyl 4-[3-(1-naphthyloxy)propylamino]benzoate and 3.4 g. of 85% KOH in 75 ml. 95% ethanol is heated at 80° C. for 4 hours, the reaction then diluted with 150 ml. of water and adjusted to pH 3 with 37% HCl. The resulting oily solid is extracted using several portions of warm ether. The extracts are combined, dried, and evaporated to a solid which is crystallized from acetonitrile to yield crystals, m.p. 146°-147° C.

Workup

  1. customthe reaction
  2. additionthen diluted with 150 ml
  3. extractionThe resulting oily solid is extracted
  4. customdried
  5. customevaporated to a solid which
  6. customis crystallized from acetonitrile
  7. customto yield crystals, m.p. 146°-147° C.

Sources & evidence

ORD record
ord-7158fb1b16cf4e69bbe8f7fd5deabcdb
Source dataset
uspto-grants-1981_04
Patent number
US04260816

Reaction notes

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