2-Methyl-3-butyn-2-ol → 3-Butyn-2-ol, 4-(3-aminophenyl)-2-methyl-

HRID 1075491Notes

Reaction equation

HRID 1075491 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:9][C:10]([OH:14])([C:12]#[CH:13])[CH3:11].CN(C)C(N(C)C)=N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>Cl[Cu].Cl[Pd]Cl.C(Cl)Cl.O.CN(C)C=O>[NH2:5][C:4]1[CH:3]=[C:2]([C:13]#[C:12][C:10]([CH3:11])([OH:14])[CH3:9])[CH:8]=[CH:7][CH:6]=1

Participants

10

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 115623-BromoanilineHCID 11776TriphenylphosphineHCID 664601,1,3,3-Tetramethylguanidine

Product 1

HCID 1122363-Butyn-2-ol, 4-(3-aminophenyl)-2-methyl-Yield 71%

Reagents, catalysts & solvents 5

HCID 24290Palladium ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A 250 ml round bottomed flask fitted with refrigerator, under nitrogen stream, is loaded with 3-bromoaniline (16 ml), dimethylformamide (80 ml), 2-methyl-3-butyn-2-ol (21.3 ml), 1,1,3,3-tetramethyl guanidine (20.3 ml), CuCl (0.044 g), PdCl2 (0.156 g) and triphenyl phosphine (0.925 g), in this order. The mixture is heated to 70°-75° C., keeping this temperature until completion of the reaction. H2O (250 ml) and CH2Cl2 (100 ml) are added at a temperature of 35°-30° C. The organic phase is dried, then evaporated to dryness. The residue is purified by chromatography to obtain 18.5 g of 4-(3-aminophenyl)-2-methyl-3-butyn-2-ol. Yield: 71% with HPLC purity ≥99%.

Workup

  1. customA 250 ml round bottomed flask fitted with refrigerator, under nitrogen stream
  2. temperatureThe mixture is heated to 70°-75° C.
  3. customuntil completion of the reaction
  4. customThe organic phase is dried
  5. customevaporated to dryness
  6. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-72bbd8b050cd44f987baabc0453b7295
Source dataset
uspto-grants-1999_05
Patent number
US05902902

Reaction notes

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