Aniline → Ammonium Hydroxide

HRID 2118670Notes

Reaction equation

HRID 2118670 reaction equation
[C:1]1([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:21]#[N:22])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[OH-:11].[NH4+:20].[C:23]1([N:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[C:21]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[NH:22])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 13957311HCID 13957311, compound

Product 2

HCID 14923Ammonium HydroxideHCID 178512001HCID 178512001, compound

Procedure

5.25 Grams of 1-(1-naphthyloxy)-8-(phenylcyanoamino)octane and 15 ml of aniline were heated at 170° for 45 min. The excess aniline was removed under vacuum and the residue was chromatographed on a silica gel column eluting with a mobile phase of methylene chloride: methanol:ammonium hydroxide, 50:30:0.3, affording the title compound, (mp 132°-134° as the paratoluene sulphonate).

Workup

  1. customThe excess aniline was removed under vacuum
  2. customthe residue was chromatographed on a silica gel column
  3. washeluting with a mobile phase of methylene chloride

Sources & evidence

ORD record
ord-351796099d8a4e8795a769bc86737241
Source dataset
uspto-grants-1987_07
Patent number
US04680300

Reaction notes

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