1-Bromonaphthalene → HCID 14502047, compound

HRID 231859Notes

Reaction equation

HRID 231859 reaction equation
[C:1]1(Br)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Mg].[Mg].BrC1C2C(=CC=CC=2)C=CC=1.[CH2:25]([N:27]([CH2:41][CH3:42])[CH2:28][CH2:29][N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40])[CH3:26]>O1CCCC1>[CH2:41]([N:27]([CH2:25][CH3:26])[CH2:28][CH2:29][N:30]1[C:34]([OH:35])([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[C:33]2[C:32](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:31]1=[O:40])[CH3:42]

Participants

6

Reactant 4

HCID 70011-BromonaphthaleneHCID 437251HCID 437251, compoundHCID 5462224MagnesiumHCID 66964988HCID 66964988, compound

Product 1

HCID 14502047HCID 14502047, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a tetrahydrofuran solution of magnesium 1-naphthylbromide prepared from 1.22 g of metallic magnesium and 10.35 g of α-bromonaphthalene in 50 ml of tetrahydrofuran was added a solution of 6.16 g of N-(2-diethylaminoethyl)-phthalimide in 10 ml of tetrahydrofuran under ice cooling. After stirring for 2 hours under ice cooling, the mixture was concentrated under reduced pressure. To the residue were added 6.61 g of ammonium sulfate, 100 ml of ethyl ether and 100 ml of water. After shaking, the aqueous layer was discarded and 100 ml of water was added to the organic layer. The pH was adjusted to 1.5 with 4N-hydrochloric acid. After shaking, the organic layer was discarded and 100 ml of ethyl ether was added to the aqueous layer. The pH was adjusted to 11.5 with 10N-sodium hydroxide solution. After shaking, the aqueous layer was discarded. After the organic layer was washed with saturated aqueous sodium chloride solution, the organic layer was dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The crude crystals obtained were recrystallized from diisopropyl ether to give 2.85 g of 2-(2-diethylaminoethyl)-3-hydroxy-3-(1-naphthyl)isoindolin-1-one (Compound 20).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionTo the residue were added 6.61 g of ammonium sulfate, 100 ml of ethyl ether and 100 ml of water
  3. stirringAfter shaking
  4. addition100 ml of water was added to the organic layer
  5. stirringAfter shaking
  6. addition100 ml of ethyl ether was added to the aqueous layer
  7. stirringAfter shaking
  8. washAfter the organic layer was washed with saturated aqueous sodium chloride solution
  9. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated to dryness under reduced pressure
  11. customThe crude crystals obtained
  12. customwere recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-3660f6bd8f5a4096af49ce16d4cf6df6
Source dataset
uspto-grants-1989_07
Patent number
US04849441

Reaction notes

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