Water → HCID 54083854, compound

HRID 2231651Notes

Reaction equation

HRID 2231651 reaction equation
B.[NH2:2][C:3]1[C:11]([CH3:12])=[CH:10][C:9]([I:13])=[CH:8][C:4]=1[C:5](O)=[O:6].O.[OH-].[Na+]>C1COCC1>[NH2:2][C:3]1[C:11]([CH3:12])=[CH:10][C:9]([I:13])=[CH:8][C:4]=1[CH2:5][OH:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6331BoraneHCID 14798Sodium HydroxideHCID 112312332-Amino-5-iodo-3-methylbenzoic Acid

Product 1

HCID 54083854HCID 54083854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of borane in THF (270 cm3 of a 1M solution) was added over 0.5 hours to a stirred suspension of 2-amino-5-iodo-3-methylbenzoic acid (18.48 g) in THF (400 cm3) at 0°. After stirring at 0° for 0.5 hours, the reaction mixture was warmed to 50° for a further 3 hours. After cooling in an ice-bath, water (25 cm3) was cautiously added dropwise with stirring, the resulting mixture was treated with an aqueous 10% solution of sodium hydroxide (100 cm3), and stirring was continued for a further 24 hours. Volatile material was then removed in vacuo and the residue was partitioned between water (100 cm3) and chloroform (200 cm3). The aqueous phase was re-extracted with chloroform (2×200 cm3), and the combined and dried (MgSO4) organic extracts were evaporated in vacuo to give an oil which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with chloroform. Combination and evaporation of appropriate fractions afforded the title compound, m.p. 101°-103° (14.22 g).

Workup

  1. temperaturethe reaction mixture was warmed to 50° for a further 3 hours
  2. temperatureAfter cooling in an ice-bath
  3. stirringwith stirring
  4. stirringstirring
  5. waitwas continued for a further 24 hours
  6. customVolatile material was then removed in vacuo
  7. customthe residue was partitioned between water (100 cm3) and chloroform (200 cm3)
  8. extractionThe aqueous phase was re-extracted with chloroform (2×200 cm3)
  9. dry with materialdried (MgSO4) organic extracts
  10. customwere evaporated in vacuo
  11. customto give an oil which
  12. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  13. washeluting with chloroform
  14. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-98a957712c1c4cf7ab3bb1aaecd64221
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

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