Water → HCID 54200497, compound

HRID 1531763Notes

Reaction equation

HRID 1531763 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH2:12].Br[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].O.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][CH2:14][NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH2:12])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 136481,2-NaphthalenediamineHCID 68320Ethyl 3-bromopropionateHCID 516892Sodium Bicarbonate

Product 1

HCID 54200497HCID 54200497, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of VII (11.4 g, 58 mmol) and ethyl 3-bromopropionate (7.5 mL, 58 mmol) in DMF (120 mL) was heated to 50° C. for 8 h. The reaction mixture was poured into water and neutralized with NaHCO3. The products were extracted into CH2Cl2 (2×200 mL). The combined organics were washed with water (4×200 mL) and dried over Na2SO4. The solvent was evaporated in vacuo and the products separated by flash chromatography using 27% EtOAc in hexane as the eluant to give the product VIII, 2.60 g (17%) as a brown solid: MS m/z 259 (MH+); 1H NMR (DMSO-d6) δ 1.22 (t, 3H), 2.64 (t, 2H), 3.09 (br t, 2H), 4.05 (br s, 1H), 4.09 (q, 2H), 5.19 (br s, 2H), 7.04 (d, 1H), 7.13 (dd, 1H), 7.33 (dd, 1H), 7.40 (d, 1H), 7.66 (d, 1H) and 7.97 (d, 1H); and the product XII, 2.06 g (13%) as a brown solid: MS m/z 259 (MH+); H NMR (DMSO-d6) d 1.21 (t, 3H), 2.63 (t, 2H), 3.43 (br m, 2H), 4.10 (q, 2H), 4.65 (br s, 1H), 4.97 (br s, 2H), 7.04 (d, 1H), 7.11-7.18 (m, 2H), 7.27 (dd, 1H), 7.62 (d, 1H), and 7.94 (d, 1H)

Workup

  1. extractionThe products were extracted into CH2Cl2 (2×200 mL)
  2. washThe combined organics were washed with water (4×200 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated in vacuo
  5. customthe products separated by flash chromatography

Sources & evidence

ORD record
ord-0c114437b2b64649a66a360635f4536a
Source dataset
uspto-grants-2001_03
Patent number
US06200984B1

Reaction notes

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