Formaldehyde → 1208091-01-3

HRID 1014385Notes

Reaction equation

HRID 1014385 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:10].[CH2:11]=O.C[O-].[Na+].[BH4-].[Na+]>CO.C(OCC)(=O)C>[CH3:11][NH:10][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 76102-Methyl-4-methoxyanilineHCID 4311764Sodium borohydrideHCID 10942334Sodium Methoxide

Product 1

HCID 145678141208091-01-3Yield 91.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of [2-methyl-4-(methyloxy)phenyl]amine (5 ml, 39.2 mmol), paraformaldehyde (5.88 g, 196 mmol), and sodium methoxide (10.58 g, 196 mmol) in methanol (100 ml) was maintained at 50° C. for 5 hours, cooled, and sodium borohydride (7.41 g, 196 mmol) was added portionwise. The resulting suspension was re-heated to 50° C. and maintained for 16 hours. The reaction was cooled, poured into ethyl acetate/saturated sodium bicarbonate, and the organic layer was dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by column chromatography to afford N,2-dimethyl-4-(methyloxy)aniline (5.40 g, 35.7 mmol, 91% yield) as a pale orange oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.55-6.68 (m, 2 H), 6.34-6.40 (m, 1 H), 4.47-4.66 (m, 1 H), 3.62 (s, 3 H), 2.66 (d, J=5.0 Hz, 3 H), 2.04 (s, 3 H).

Workup

  1. temperaturecooled
  2. temperatureThe resulting suspension was re-heated to 50° C.
  3. temperaturemaintained for 16 hours
  4. temperatureThe reaction was cooled
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-8092586925c54cfb88c9bd4dbcf0fc53
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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