Methyl 2-formylbenzoate → HCID 14748254, compound

HRID 1165196Notes

Reaction equation

HRID 1165196 reaction equation
[CH3:1][C:2]1([CH3:17])[C@@H:7]([OH:8])[C@H:6]([NH2:9])[C:5]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:4]=2[O:3]1.[C:18]([C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=O)(OC)=[O:19].C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:1][C:2]1([CH3:17])[C@@H:7]([OH:8])[C@H:6]([N:9]2[CH2:24][C:23]3[C:22](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:18]2=[O:19])[C:5]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:4]=2[O:3]1

Participants

6

Reactant 3

HCID 243003Methyl 2-formylbenzoateHCID 5003444Sodium cyanoborohydrideHCID 14748252HCID 14748252, compound

Product 1

HCID 14748254HCID 14748254, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

To 351 mg (1.48 mmol) of trans-3,4-dihydro-2,2-dimethyl-3-hydroxy-7-nitro-2H-1-benzopyran-4-amine in methanol (3 mL) containing 290 mg (1.77 mmol) of 2-carbomethoxybenzaldehyde was added 1.5 mL (0.75 mmol) of 0.5M zinc chloride-modified sodium cyanoborohydride in methanol, prepared according to the method of Kim et al. J. Org. Chem. 50 (11), 1927 (1985). After stirring at 50° C. for two days, the reaction mixture was quenched with saturated NaHCO3 solution, extracted into CH2Cl2, dried (K2CO3) and concentrated. The residue was dissolved in a minimal amount of THF and silica gel was added. The solvent was removed in vacuo and the silica gel was applied onto the head of a flash column. Eluting with 20%→50% ether/CH2Cl2 gave 390 mg of the title compound as a pale yellow powder, m.p. 249°-250° C.

Workup

  1. customprepared
  2. customthe reaction mixture was quenched with saturated NaHCO3 solution
  3. extractionextracted into CH2Cl2
  4. dry with materialdried (K2CO3)
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in a minimal amount of THF and silica gel
  7. additionwas added
  8. customThe solvent was removed in vacuo
  9. washEluting with 20%→50% ether/CH2Cl2

Sources & evidence

ORD record
ord-25f18a006a16426cbc23a8a933b8d07d
Source dataset
uspto-grants-1990_03
Patent number
US04908378

Reaction notes

Loading…