Ethyl 2-aminobenzoate → Ethyl 2-{[2-(1-naphthyloxy)ethyl]amino}benzoate

HRID 443652

Reaction equation

HRID 443652 reaction equation
[C:1]1([O:11][CH2:12][CH2:13]Br)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:15]([O:24][CH2:25][CH3:26])(=[O:23])[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH2:18].CN(C)P(N(C)C)(N(C)C)=O>O>[C:1]1([O:11][CH2:12][CH2:13][NH:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[C:15]([O:24][CH2:25][CH3:26])=[O:23])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6877Ethyl 2-aminobenzoateHCID 12679HexamethylphosphoramideHCID 110759061-(2-Bromoethoxy)naphthalene

Product 1

HCID 23468271Ethyl 2-{[2-(1-naphthyloxy)ethyl]amino}benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 12.54 g. of 2-(1-naphthyloxy)ethyl bromide and 16.5 g. of ethyl anthranilate in 50 ml. of hexamethylphosphoramide are heated at 110° for 18 hours. After cooling and diluting with water, the mixture is extracted twice with 200 ml. of ether. The combined ether extracts are washed with water, dried and evaporated to a brown oil. The oil is dissolved in 60 ml. of ethanol and chilled in an ice-bath yielding a beige solid which is recrystallized from 100 ml. of ethanol affording pale yellow crystals, m.p. 81°-83° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted twice with 200 ml
  3. washThe combined ether extracts are washed with water
  4. customdried
  5. customevaporated to a brown oil
  6. dissolutionThe oil is dissolved in 60 ml
  7. temperatureof ethanol and chilled in an ice-bath
  8. customyielding a beige solid which
  9. customis recrystallized from 100 ml

Sources & evidence

ORD record
ord-c6c19d9a1f554ed29db948a37fd82ba5
Source dataset
uspto-grants-1981_04
Patent number
US04260816

Linked notes

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