Ammonia → HCID 178464433, compound

HRID 1390084Notes

Reaction equation

HRID 1390084 reaction equation
[Cl-].[CH2:2]([N:4]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]#[N:15])=[CH:10][CH:9]=1)[CH2:5][CH2:6][OH:7])[CH3:3].S(=O)(=O)(O)O.[CH2:21]([N:23]([CH2:31][CH2:32][OH:33])[C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1)[CH3:22].Cl.N([O-])=O.[Na+].[CH:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:42]=[C:41]([OH:49])[C:40]=1[OH:50].[NH3:51]>O.N1C=CC=CC=1>[CH2:2]([N:4]([C:8]1[CH:13]=[CH:12][C:11]([N:14]=[N:15][C:42]2[C:43]3[C:48](=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:39]([N:51]=[N:30][C:27]3[CH:28]=[CH:29][C:24]([N:23]([CH2:31][CH2:32][OH:33])[CH2:21][CH3:22])=[CH:25][CH:26]=3)=[C:40]([OH:50])[C:41]=2[OH:49])=[CH:10][CH:9]=1)[CH2:5][CH2:6][OH:7])[CH3:3]

Participants

9

Reactant 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 70912,3-DihydroxynaphthaleneHCID 67259Benzenediazonium, 4-[ethyl(2-hydroxyethyl)amino]-, chloride (1:1)HCID 275652914623-68-8HCID 23668193Sodium Nitrite

Product 1

HCID 178464433HCID 178464433, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

A solution of 0.200 mole of p-(N-ethyl-N-2-hydroxyethylamino)benzenediazonium chloride (made as in the following procedure: To a stirred solution of 0.200 g. mole of N-ethyl-N-2-hydroxyethyl-p-phenylenediamine bisulfate, 0.80 g. mole of concentrated hydrochloric acid and 400 ml. of distilled water was added dropwise with stirring at 0°-10° C. a solution of 0.20 g. mole of sodium nitrite in water.) was added dropwise with stirring at 0°-5° C. to a solution of 15.9 g. (0.0994 mole) of 2,3-naphthalenediol, 400 ml. of pyridine and 150 ml. of aqueous 28% ammonia. The mixture was stirred for 11/2 hr. after completion of the addition. The solid was collected, washed with methanol and then water, and dried in vacuum at 45° C. to give 42.3 g. of green product, m.p. 240° C. Recrystallization from 400 ml. of pyridine gave 33.2 g. (61.6%) of green crystals, m.p. 247° C. (dec.),

Workup

  1. addition) was added dropwise
  2. stirringwith stirring at 0°-5° C. to a solution of 15.9 g
  3. stirringThe mixture was stirred for 11/2 hr
  4. additionafter completion of the addition
  5. customThe solid was collected
  6. washwashed with methanol
  7. dry with materialwater, and dried in vacuum at 45° C.
  8. customto give 42.3 g
  9. customRecrystallization from 400 ml
  10. customof pyridine gave 33.2 g

Sources & evidence

ORD record
ord-75a4b22d44dd4b9db6a7dc40a911765d
Source dataset
uspto-grants-1981_01
Patent number
US04247459

Reaction notes

Loading…