Water → 3-(3-Aminonaphthalen-2-ylamino)propionic acid ethyl ester

HRID 1531762Notes

Reaction equation

HRID 1531762 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.Br[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].O>CN(C=O)C>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][CH2:14][NH:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1)[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 68320Ethyl 3-bromopropionateHCID 698722,3-Diaminonaphthalene

Product 1

HCID 155120243-(3-Aminonaphthalen-2-ylamino)propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,3-diaminonaphthalene (14.3 g, 90.4 mmol) and ethyl 3-bromopropionate (14 mL, 0.108 mol) in DMF (150 mL) was heated to 50° C. for 24 h. The reaction mixture was poured into water (600 mL) and the product was extracted into CH2Cl2 (2×200 mL). The combined organics were washed three times with water and dried over Na2SO4. The solvent was evaporated in vacuo and the resultant residue was purified by flash chromatography using 27% to 40% EtOAc in hexane as the eluant to give the product as a brown solid, 7.6 g (33%): MS m/z 259 (MH+); 1H NMR (DMSO-d6) δ 1.22 (t, 3H), 2.73 (t, 2H), 3.37-3.45 (m, 2H), 4.12 (q, 2H), 5.03 (br s, 2H), 5.09 (br t, 1H), 6.71 (s, 1H), 6.85 (s, 1H), 6.98-7.05 (m, 2H), 7.36-7.43 (m, 1H) and 7.47-7.53 (m, 1H).

Workup

  1. extractionthe product was extracted into CH2Cl2 (2×200 mL)
  2. washThe combined organics were washed three times with water
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated in vacuo
  5. customthe resultant residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a52d62490eaa462e982a5890f3be5454
Source dataset
uspto-grants-2001_03
Patent number
US06200984B1

Reaction notes

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