Methyl 1-amino-4-bromo-2-naphthoate hydrobromide → Methyl 1-amino-4-(4-methoxybenzyl)-2-naphthoate

HRID 1042298Notes

Reaction equation

HRID 1042298 reaction equation
Br.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([Br:13])=[CH:5][C:4]=1[C:14]([O:16][CH3:17])=[O:15].[Cl-].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][Zn+])=[CH:23][CH:22]=1>C(OCC)(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[BrH:13].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([Br:13])=[CH:5][C:4]=1[C:14]([O:16][CH3:17])=[O:15].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:25][C:24]2[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)=[CH:5][C:4]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

7

Reactant 2

HCID 66979039Methyl 1-amino-4-bromo-2-naphthoate hydrobromideHCID 178490612HCID 178490612, compound

Product 2

HCID 58431854Methyl 1-amino-4-(4-methoxybenzyl)-2-naphthoateHCID 66979039Methyl 1-amino-4-bromo-2-naphthoate hydrobromide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 1-amino-4-bromo-2-naphthoate hydrobromide was prepared as described in Example 1. To a round bottom flask containing methyl 1-amino-4-bromo-2-naphthoate hydrobromide (3.50 g, 9.69 mmol) under an atmosphere of nitrogen was added 4-methoxybenzylzinc chloride (97.0 mL, 0.5 M in THF, 48.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (10 mol %). The mixture was heated at 90° C. for 7 h, cooled to rt, and diluted with 50 mL of ethyl acetate and 50 mL of water. The mixture was partitioned and the organic extract was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-20% ethyl acetate in hexanes, to provide methyl 1-amino-4-(4-methoxybenzyl)-2-naphthoate that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 322.0 for [M+H]+.

Workup

  1. temperaturecooled to rt
  2. customThe mixture was partitioned
  3. extractionthe organic extract
  4. washwas washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via silica gel chromatography
  9. washeluting with 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-cc1d66a381784d5796a25b58ead96702
Source dataset
uspto-grants-2013_10
Patent number
US08557832B2

Reaction notes

Loading…