Tert-Butylamine → HCID 21824657, compound

HRID 886771Notes

Reaction equation

HRID 886771 reaction equation
C(N)(C)(C)C.[Br:6]N1C(=O)CCC1=O.[CH3:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[C:18]([OH:25])[CH:19]=[CH:20][CH:21]=2)[N:16]=1>C1(C)C=CC=CC=1.CCCCCC>[Br:6][C:19]1[C:18]([OH:25])=[C:17]2[C:22]([CH:23]=[CH:24][C:15]([CH3:14])=[N:16]2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 132242-Methyl-8-hydroxyquinolineHCID 67184N-bromobutanimide

Product 1

HCID 21824657HCID 21824657, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

The protocol was established from works by: D. E. Pearson et al. J. Org. Chem. 1967, 2358-2360. tert-butylamine (3.23 ml, 30.78 mmol) is stirred under argon in 100 ml of toluene for 2 hours at ambient temperature in the presence of an activated 4 Å molecular sieve (10 g). After cooling to −70° C., N-bromosuccinimide (5.48 g; 30.78 mmol) and 2-methyl-8-hydroxyquinoline (5.00 g; 30.78 mmol) are added in succession. The mixture is slowly brought to ambient temperature (approximately 4 hours). The reaction medium is filtered and the molecular sieve is washed with diethyl ether (20 ml). The filtrate is washed in water (3×50 ml), dried over anhydrous Na2SO4 and the organic phase is concentrated to yield a solid which is brought to reflux in 100 ml of hexane for 1 hour. After 24 hours at ambient temperature, the precipitate is filtered and dried under vacuum to yield 7-bromo-2-methyl-8-hydroxyquinoline in the form of a white powder (4.85 g; 20.47 mmol, yield=67%). NMR-1H (250 MHz, CDCl3) δ, ppm: 8.00 (d, 3J (H, H)=8.5 Hz, 1H); 7.52 (d, 3J (H, H)=9.0 Hz, 1H); 7.31 (d, 3J (H, H)=8.5 Hz, 1H); 7.16 (d, 3J (H, H)=9.0 Hz, 1H); 2.72 (s, 3H). NMR-13C (63 MHz, CDCl3) δ, ppm: 157.9; 149.2; 137.7; 136.2; 130.1; 125.4; 122.9; 118.2; 103.9; 24.8. MS (CID, NH3): m/z=238 (MH+). Analysis (%) for C10H8BrNO: calculated C, 50.45. H, 3.39. N, 5.88. found C, 50.02. H, 3.37. N, 6.12.

Workup

  1. customis slowly brought to ambient temperature
  2. custom(approximately 4 hours)
  3. filtrationThe reaction medium is filtered
  4. washthe molecular sieve is washed with diethyl ether (20 ml)
  5. washThe filtrate is washed in water (3×50 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationthe organic phase is concentrated
  8. customto yield a solid which
  9. filtrationthe precipitate is filtered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-858cea390f7347a1b3a0c40b95306740
Source dataset
uspto-grants-2012_08
Patent number
US08247396B2

Reaction notes

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