Ammonium formate → (5-Amino-2-morpholinophenyl)methanol

HRID 1190918Notes

Reaction equation

HRID 1190918 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=2[CH2:16][OH:17])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[C:8]([CH2:16][OH:17])[CH:9]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 2727950HCID 2727950, compound

Product 1

HCID 23136616(5-Amino-2-morpholinophenyl)methanolYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

[2-(Morpholin-4-yl)-5-nitrophenyl]methanol (1.38 g, 5.80 mmol) was hydrogenated using ammonium formate (3.67 g, 58 mmol) and Pd/C (10% Pd, 0.62 g, 0.58 mmol) in 50 mL of EtOH. The mixture was stirred for 1 h at room temperature and then filtered through a celite pad. The filtrate was evaporated and the residue was dissolved in DCM and washed with a saturated aqueous solution of Na2CO3. The aqueous layer was extracted with DCM. The combined organic layers were dried over MgSO4, filtered and evaporated to yield expected compound as a brown powder (1.21 g, 99% yield). LC-MS: m/z (ESI) 209.2 [M+H]+. 1H NMR (300 MHz, MeOH-d4) δ7.02; (d, J=15.0 Hz, 1H), 6.83; (d, J=9.0 Hz, 1H), 6.68; (dd, J=6.0 Hz, 1H), 4.71; (s, 2H), 3.82; (t, J=4.5 Hz, 4H), 2.87; (t, J=4.7 Hz, 4H).

Workup

  1. filtrationfiltered through a celite pad
  2. customThe filtrate was evaporated
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with a saturated aqueous solution of Na2CO3
  5. extractionThe aqueous layer was extracted with DCM
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-d5b5b291b85d4439aed6400d594910b8
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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