Ammonium formate → HCID 54335918, compound

HRID 572702Notes

Reaction equation

HRID 572702 reaction equation
[CH2:1]([O:8][C:9]1[CH:36]=[CH:35][C:12]([CH:13]([OH:34])[CH2:14][N:15]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:16]([CH3:26])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:11][C:10]=1[N+:37]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>CN(C=O)C.[Pd]>[NH2:37][C:10]1[CH:11]=[C:12]([CH:35]=[CH:36][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:13]([OH:34])[CH2:14][N:15]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:16]([CH3:26])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 9914834α-[[[2-(4-Methoxyphenyl)-1-methylethyl](phenylmethyl)amino]methyl]-3-nitro-4-(phenylmethoxy)benzenemethanol

Product 1

HCID 54335918HCID 54335918, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-benzyloxy-3-nitro-α-[N-benzyl-N-(1-methyl-2-p-methoxyphenylethyl)aminomethyl]benzyl alcohol (100 gms, 0.19 M) in DMF (500 ml) was added 10% Pd/C. The resulting mass was heated to 40° C. and ammonium formate (36 gms, 0.57 M) was added in lots in 1 hour. The reaction mass was heated slowly to 70-75° C. for 1 hour, then cooled to 50° C. The catalyst was removed by filtration and the clear filtrate evaporated. The residue was stirred in water (500 ml) and basified with liq. Ammonia. The reaction mass was extracted in 1.0-lit toluene, washed organic extract with water, dried on sodium sulfate and evaporated to obtain title compound. (80 gms, 84.21%)

Workup

  1. temperatureThe reaction mass was heated slowly to 70-75° C. for 1 hour
  2. temperaturecooled to 50° C
  3. customThe catalyst was removed by filtration
  4. customthe clear filtrate evaporated
  5. extractionThe reaction mass was extracted in 1.0-lit toluene
  6. washwashed organic
  7. extractionextract with water
  8. customdried on sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-6b5ba3c709104630a1c187e1d581476b
Source dataset
uspto-grants-2015_05
Patent number
US09029421B2

Reaction notes

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