Dihydrocaffeic acid → HCID 18455701, compound

HRID 1272456Notes

Reaction equation

HRID 1272456 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[OH:17][C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][C:28]=1[OH:29])[CH2:21][CH2:22][C:23](O)=[O:24]>>[OH:17][C:18]1[CH:19]=[C:20]([CH2:21][CH2:22][C:23]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:24])[CH:26]=[CH:27][C:28]=1[OH:29]

Participants

3

Reactant 2

HCID 348154Dihydrocaffeic acidHCID 7359662-(2-Aminophenyl)indole

Product 1

HCID 18455701HCID 18455701, compoundYield 19%

Procedure

Prepared from 2-(2-aminophenyl) indole and 3,4-dihydroxyhydrocinnamic acid in 19% yield following procedure 1. The product was chromatographed on silica and crystallized from acetonitrile. 100% Purity by LC/MS (230 DAD), Mass-spec [M+H+]=373, 1H NMR (MeOH-d4): 2.60 t, 7.4 Hz (2H), 2.85 t, 7.4 Hz (2H), 6.38 s (1H), 6.55 dd, 8.2 Hz (1H), 6.69 m (2H), 7.02 t, 8 Hz (1H), 7.11 t, 8 Hz (1H), 7.27–7.35 m (2H), 7.38 d, 8 Hz (1H), 7.56 d, 8 Hz (1H), 7.58 dd, 7.1 Hz (1H), 7.70 d, 8 Hz (1H).

Workup

  1. customThe product was chromatographed on silica
  2. customcrystallized from acetonitrile
  3. customby LC/MS (230 DAD), Mass-spec [M+H+]=373, 1H NMR (MeOH-d4): 2.60 t, 7.4 Hz (2H), 2.85 t, 7.4 Hz (2H), 6.38 s (1H), 6.55
  4. custom8.2 Hz (1H), 6.69 m (2H), 7.02 t, 8 Hz (1H), 7.11 t, 8 Hz (1H), 7.27–7.35 m (2H), 7.38 d, 8 Hz (1H), 7.56 d, 8 Hz (1H), 7.58
  5. custom7.1 Hz (1H), 7.70 d, 8 Hz (1H)

Sources & evidence

ORD record
ord-dfa19a5b0e68456e8201472f54349bbc
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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