Methylamine → HCID 66752023, compound

HRID 1785406Notes

Reaction equation

HRID 1785406 reaction equation
[CH3:1][N:2]([CH:4]=[C:5]1[C:10]2=[N:11][C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:17]=3[CH:18]=[C:9]2[C:8](=[O:19])[O:7][C:6]1=[O:20])C.CN>>[CH3:1][N:2]1[CH:4]=[C:5]([C:6]([OH:7])=[O:20])[C:10]2[N:11]=[C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:17]3=[CH:18][C:9]=2[C:8]1=[O:19]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 86601401HCID 86601401, compound

Product 1

HCID 66752023HCID 66752023, compound

Procedure

From 17e and methylamine, as for 18d except that, after reaction, the volatiles were removed at reduced pressure and water was added. The resultant suspension was stirred and basified with 10% sodium hydroxide, then acidified with concentrated hydrochloric acid (dropwise) and the brown solid was filtered to give 18y, mp >300° C. (from dimethyl sulfoxide/1,4-dioxane). 1H NMR (d6-DMSO): δ 3.64 (s, 3H, NCH3), 7.76 (dd, J=8.2, 4.2 Hz, 1H, H-3), 8.81 (d, J=8.2 Hz, 1H, H-4), 8.85 (s, 1H, H-8), 9.28 (dd, J=3.9, 1.7 Hz, 1H, H-2), 9.58 (s, 1H, H-5), 15.68 (s, 1-H, COOH).

Workup

  1. customthe volatiles were removed at reduced pressure and water
  2. additionwas added
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-5607a5ae052246579c0ccc31910e8da9
Source dataset
uspto-grants-2009_03
Patent number
US07504507B2

Reaction notes

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