5-Aminosalicylic Acid → HCID 42599838, compound

HRID 1943510Notes

Reaction equation

HRID 1943510 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C(N(CC)CC)C.[Br:19][C:20]([CH3:25])([CH3:24])[C:21](Br)=[O:22]>C1(C)C=CC=CC=1>[Br:19][C:20]([CH3:25])([CH3:24])[C:21]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8])=[O:22]

Participants

5

Reactant 3

HCID 40755-Aminosalicylic AcidHCID 8471TriethylamineHCID 886852-Bromo-2-methylpropionyl bromide

Product 1

HCID 42599838HCID 42599838, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 5-amino-2-hydroxybenzoic acid (3.0 g, 19.6 mmol) in a solution of freshly distilled triethylamine (4.1 mL, 29.4 mmol, 1.5 eq.) in 100 mL of anhydrous toluene was added dropwise 2-bromoisobutyryl bromide (6.8 mL, 53.8 mmol). Addition was performed at 0° C. under inert atmosphere. The mixture was then refluxed for 15 hours. Volatiles were removed under vacuum leaving oily crude materials. The product initiator C was extracted with ethanol concentrated and crystallized at −30° C. Yield: 30%. Analysis: 1H NMR (CDCl3, 300 MHz, 298 K): δ 9.81 (s broad, 3H, NHCO and OH), 8.24 (s, 1H, Hortho), 7.76 (d, 1J=10.5 Hz, 1H, Hmeta), 6.82 (d, 1J=9.8 Hz, 1H, Hpara), 2.10 (s, 6H, Me). 13C NMR (CDCl3, 125 MHz, 298 K): δ 170.6 (CO—N), 167.2 (CO—O), 160.0 (C(aromatic)-OH), 130.8 (C(aromatic)-NH), 124.1 (C(aromatic)-H), 122.2 (C(aromatic)-H), 118.6 (C(aromatic)-H), 114.2 (C(aromatic)-CO2H), 58.9 (C—Br), 33.6 (CH3), confirming the product to be 5-(2-bromo-2-methylpropanamido)-2-hydroxybenzoic acid initiator (initiator C).

Workup

  1. additionAddition
  2. customwas performed at 0° C. under inert atmosphere
  3. temperatureThe mixture was then refluxed for 15 hours
  4. customVolatiles were removed under vacuum
  5. customleaving oily crude materials
  6. extractionThe product initiator C was extracted with ethanol
  7. concentrationconcentrated
  8. customcrystallized at −30° C

Sources & evidence

ORD record
ord-8d8f15a3e5ca4a9796cc98d677c7e96e
Source dataset
uspto-grants-2013_03
Patent number
US08394022B2

Reaction notes

Loading…